United States Patent Office Patented May 16, 1967 2 3,320,314 125 C

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3,320,314 United States Patent Office Patented May 16, 1967 2 3,320,314 125 C. Agitation may be employed during the reaction, CHLOROBENZYL SULFAMDES but none is required. William J. Houlihan, Mountain Lakes, N.J., assignor to The tertiary amine medium provides a solvent system Sandoz Inc., Hanover, N.J. in which the reaction takes place. Contemplated tertiary No Drawing. Filled June 15, 1964, Ser. No. 375,288 5 amines include, for example, tri(lower) alkylamines, e.g. 6 Claims. (C. 260-556) triethylamine; (lower) alkyl pyrroles, e.g. N-propyl-pyr This application is a continuation-in-part of application role; pyridine; (lower) alkyl pyridines, e.g. 3-ethyl pyri Ser. No. 339,354, filed on Jan. 22, 1964, and now aban dine; (lower) alkoxy pyridines, e.g. 2,5-dimethoxypyri doned. dine; quinoline; (lower) alkyl quinolines, e.g. 8-ethyl O quinoline; N-(lower) alkyl morpholine, e.g. N-methyl This invention is directed to two groups of benzyl sulf morpholine; and N,N'-di(lower) alkyl piperazine, e.g. amides having one or more chlorine substituents on the N-methyl,N'-ethyl-piperazine. sole aromatic ring. These groups are, respectively, of For the preparation of Compounds II wherein R6 is a the formulae hydrogen atom similar reaction conditions are employed; R1 a primary benzyl amine (V) is substituted for the sec ondary benzyl amine (III), and the reaction medium is an R2- ceN seNH aqueous ethanolic medium: R R3- -H 20 R1 R4 (I) and R2- ot NH R1 -- (IV) - (II) -- NH3 R3 -Rs R' ce ise 25 R2- N NEI k (B) R6 R3 -R5 (V)

RA (II) 30 wherein In both reaction (A) and reaction (B) each of R, R, R is either lower alkyl having two or more carbon atoms R, R3, R, R5 and R6 has its above-ascribed meaning. e.g. ethyl, propyl and isopropyl; cyclopropyl; allyl; Compounds III and V are prepared from known starting cy-methallyi; (3-methallyl or 6,6-dimethallyl; materials according to standard art-recognized procedures. each of The temperature at which reactions (A) and (B) are conducted is usually the reflux temperature of the system. R, R2, R3, R4 and R5 is either a hydrogen atom (-H); Compounds I and I are useful as anticonvulsants and lower alkyl, e.g. methyl, ethyl, propyl, isopropyl and mild tranquilizers which may be administered either oral butyl; lower alkoxy, e.g. methoxy, ethoxy, propoxy, ly or parenterally. Oral dosage forms include tablets isopropoxy and butoxy; a fluorine atom (-F); or a 40 and capsules having standard fillers and other compound chlorine atom (-CI); at least one of R, R, R8 and ing constituents. The average daily dose may vary within Ré being a chlorine atom; and the range of from 50 milligrams to 300 milligrams. R8 is either a hydrogen atom (-H) or methyl. The following examples illustrate the invention, all tem In Formula II, in addition, at least one of R, R, R, peratures being in degrees centigrade, the parts and per R4 and R5 must be a hydrogen atom, but both R and R centages being by weight unless otherwise stated, and the can be other than hydrogen in the same molecule. In relationship between parts by weight and parts by volume Formula I there must be at least one hydrogen atom ortho being the same as that between the kilogram and the liter. to the benzyl methylene group. An object of this invention is to obtain low-cost com 50 EXAMPLE 1. pounds which have CNS (central nervous system) activity with little or no direct peripheral effects. A further ob N-methyl-N-2,4-dichloro benzylsulfanide ject is to obtain CNS depressants which possess moderate to marked anticonvulsant activity. These and further objects are accomplished by com 55 pounds of both of the above-defined groups. C- -Cl CH The preparation of Compounds I and the Compounds N-SO2NIH II wherein R6 is methyl is accomplished by heating at a N/ temperature within the range of from about 50° to 250 C. and in a tertiary amine (a) secondary benzyl amine 60 (III) and (b) sulfamide (IV): In a flask equipped with a stirrer and a condenser at R1 tached to a bubble detector dissolve 19.0 parts (0.10 CH2 mole) of N-methyl-2,4-dichloro benzylamine and 9.6 R2- / NH H.N. 65 parts (0.10 mole) of sulfamide in 100 parts by volume of | -- SO2 -}. (I) -- NH3 pyridine. Stir and reflux the resulting solution until gas R-l. 1-H HN sing is no longer detected in the bubble detector. Remove the solvent (pyridine) in vacuo on a rotary evaporator. R4 (A) Crystallize the viscous residue from methanol-water. (III) (IV) 70 There are thus obtained 18.2 parts of N-methyl-N-2,4-di A reaction temperature in excess of 50° C. is recom chlorobenzylsulfamide, melting point (M.P.) 113 to mended, and a preferred range is from about 55 to about 115. 3,320,314 3. 4 In similar manner by separately replacing the N-meth In similar manner by separately replacing the N-meth yl-N-2,4-dichlorobenzylamine by an equivalent amount of yl-3,4-dichloro-benzylamine by an equivalent amount of each of each of: N-cyclopropyl-N-o-chlorobenzylamine, N-methyl-N-chlorobenzylamine, N-cyclopropyl-N-m-chlorobenzylamine, N-methyl-N-p-chlorobenzylamine, N-cyclopropyl-N-p-chlorobenzylamine, N-methyl-N-2,3-dichlorobenzylamine, N-cyclopropyl-N-2,3-dichlorobenzylamine, N-methyl-N-2,5-dichlorobenzylamine, N-cyclopropyl-N-2,4-dichlorobenzylamine, N-methyl-N-3,5-dichlorobenzylamine, N-cyclopropyl-N-2,5-dichlorobenzylamine, N-methyl-N-2,3,4-trichlorobenzylamine, O N-cyclopropyl-N-3,4-dichlorobenzylamine, N-methyl-N-2,3,5-trichlorobenzylamine, N-cyclopropyl-N-3,5-dichlorobenzylamine, N-methyl-N-2,4,5-trichlorobenzylamine, N-cyclopropyl-N-2,3,4-trichlorobenzylamine, N-methyl-N-3,4,5-trichlorobenzylamine and N-cyclopropyl-N-2,3,5-trichlorobenzylamine, N-methyl-N-2,3,4,5-tetrachlorobenzylamine, N-cyclopropyl-N-2,4,5-trichlorobenzylamine, each of the corresponding Compounds I is obtained. 5 N-cyclopropyl-N-3,4,5-trichlorobenzylamine and N-cyclopropyl-N-2,3,4,5-tetrachlorobenzylamine, EXAMPLE 2. each of the corresponding Compounds I is obtained. N-methyl-N-o-chlorobenzyl sulfamide EXAMPLE 4 20 N-2,4-dichlorobenzyl sulfamide Cl (H, N-SO2NE Cl- Cl / H CH2 N-SO-NH2 25 N/ In a flask equipped with a stirrer and a condenser at tached to a bubble detector dissolve 12.5 parts (0.08 In a flask equipped with a stirrer, condenser and drop mole) of N-methyl-o-chlorobenzylamine and 5.8 parts ping funnel place 150 parts by volume of water, 4.8 parts (0.06 mole) of sulfamide in 100 parts by volume of (0.05 mole) of sulfamide and 8.8 parts (0.05 mole) of pyridine. Stir and reflux the resulting solution until gas 30 2,4-dichlorobenzylamine. Stir and bring the mixture to sing is no longer detected in the bubble detector. Remove reflux. Then add dropwise ethanol until a clear solution the solvent (pyridine) in vacuo on a rotary evaporator. results. Continue stirring and refluxing for 10 hours. Crystallize the viscous residue from methanol-Water. Cool to room temperature (20) and filter off the crys There are thus obtained 7.1 parts of N-methyl-N-o-chlo talline product. Crystallize from methanol-water. There robenzylsulfamide, M.P. 112 to 113. are thus obtained 6.1 parts of N-2,4-dichlorobenzylsulf In similar manner by separately replacing the N-meth amide, melting point 129 to 130. yl-o-chlorobenzylamine by an equivalent amount of each In similar manner by separately replacing the 2,4-di of: chlorobenzylamine by an equivalent amount of each of: N-o-methallyl-N-(3-chloro-2-fluoro-4-isopropyl)- 2-chloro-4,5-difluorobenzylamine, 40 2-butyl-3-chlorobenzylamine, N-6-methallyl-N-(4-chloro-3-fluoro-2-methoxy)-benzylamine, 4-chloro-2-methoxybenzylamine, N-6,6-dimethallyl-N-(2,3-dichloro-5-isopropoxy)-benzylamine, 2,3-dichlorobenzylamine,2,4-dichloro-3-ethoxy-5-fluorobenzylamine, - 2,5-dichloro-3-fluorobenzylamine, and N-methyl-N-(2-chloro-3,5-difluoro)-benzylamine,benzylamine, 2,6-dichloro-4-propoxybenzylamine, N-ethyl-N-(2,4-dichloro-3-methoxy)-benzylamine, N-propyl-N-(2,5-dichloro-4-fluoro)-benzylamine, each of the corresponding Compounds II is obtained. N-isopropyl-N-(5-butyl-3,4-dichloro)-benzylamine, EXAMPLE 5 N-allyl-N-3,4-dichlorobenzylamine, N-2-chlorobenzylsulfamide N-propyl-N-2,3,5-trichlorobenzylamine, 50 N-isopropyl-N-(3-methyl-2,4,5-trichloro)-benzylamine, Cl N-ethyl-N-3,4,5-trichlorobenzylamine and E. N-propyl-N-2,3,4,5-tetrachlorobenzylamine, N-SO-NH2 each of the corresponding Compounds I is obtained. 55 In a flask equipped with a stirrer, condenser and drop EXAMPLE 3 ping funnel place 14.1 parts (0.10 mole) of 2-chloro N-methyl-N-3,4-dichlorobenzylsulfamide benzylamine, 9.6 parts (0.10 mole) of sulfamide and 300 parts by volume of water. Stir and bring the mix Cl ture to reflux. Then add dropwise ethanol until a clear 60 Solution results. Continue stirring and refluxing for 10 hours. Cool to room temperature and filter off the crys Cl- SO-NE talline product. Crystallize from ethanol. There are N thus obtained 11.7 parts of N-2-chlorobenzylsulfamide, N/bH, melting point 95 to 96. 65 In similar manner, by separately replacing the 2-chlo In a flask equipped with a stirrer and a condenser at robenzylamine by an equivalent amount of each of: tached to a bubble detector dissolve 15.0 parts (0.08 2,3,4-trichlorobenzylamine, mole) of N-methyl-3,4-dichlorobenzylamine and 7.5 parts 2,3,5-trichlorobenzylamine, (0.08 mole) of sulfamide in 100 parts by volume of pyri 5-isopropoxy-2,3,6-trichlorobenzylamine, dine. Stir and reflux the resulting solution until gassing is 70 no longer detected in the bubble detector. Remove the 6-butoxy-2,4,5-trichlorobenzylamine, Solvent (pyridine) in vacuo on a rotary evaporator. 2,4,6-trichlorobenzylamine, Crystallize the viscous residue from methanol-water. 3-isopropyl-2,5,6-trichlorobenzylamine, and There are thus obtained 5.2 parts of N-methyl-N-3,4-di 3,4-dichlorobenzylamine, chlorobenzylsulfamide, M.P. 92 to 93. 75 each of the corresponding Compounds II is obtained. 3,320,314 5 6 EXAMPLE 6 chloro-4-methylbenzylamine by an equivalent amount of N-2,3,6-trichlorobenzylsulfamide each of: CI 3-chlorobenzylamine, 4-chlorobenzylamine, 2,5-dichlorobenzylamine, and 2,6-dichlorobenzylamine each of the corresponding Compounds II is obtained. EXAMPLE 9 O In a flask equipped with a stirrer, condenser and N-2-fluoro-5-chlorobenzylsulfamide dropping funnel, place 4.2 parts (0.02 mole) of 2,3,6-tri. chlorobenzylamine, 3.8 parts (0.4 mole) of sulfamide and 80 parts by volume of water. Stir and bring the miY E. ture to reflux. Then add dropwise ethanol until a clear 15 N-SONH2 solution results. Continue stirring and refluxing for 10 hours. Cool to room temperature and filter off the crys d talline product. Crystallize from ethanol. There are In a flask equipped with a stirrer, condenser and thus obtained 2.9 parts of N-2,3,6-trichlorobenzylsulf dropping funnel, place 8.0 parts (0.05 mole) of 2-fluoro amide, melting point 117 to 119. 20 6-chlorobenzylamine, 9.6 parts (0.10 mole) of sulfamide In similar manner by separately replacing the 2,3,6- and 75 parts by volume of water. Stir and bring the trichlorobenzylamine by an equivalent amount of each mixture to reflux. Then add dropwise ethanoi until a of: clear solution results. Continue stirring and refluxing for 3,5-dichloro-4-propylbenzylamine, 10 hours. Cool to room temperature and filter off the 3,6-dichloro-5-ethyl-2-fluorobenzylamine, and 25 crystalline product. Crystallize from ethanol. There are 6-methyl-3,4,5-trichlorobenzylamine, thus obtained 4.3 parts of N-2-fluoro-6-chlorobenzylsulf amide. each of the corresponding Compounds II is obtained. In similar manner by separately replacing the 2-fluoro EXAMPLE 7 6-chlorobenzylamine by an equivalent amount of each N-3,4-dichlorobenzylsulfamide 30 of: 2,4,5-trichlorobenzylamine, Cl 3,5-dichlorobenzylamine, and 3,4,5-trichlorobenzylamine, Cl H each of the corresponding Compounds II is obtained. N N-80NH, EXAMPLE 10 CH N-methyl-N-2,3,6-trichlorobenzylsulfamide In a flask equipped with a stirrer, condenser and dropping funnel place 11.0 parts (0.062 mole) of 3,4- 40 Gl dichlorobenzylannine, 9.6 parts (0.10 mole) of sulfamide and 150 parts by volume of water. Stir and bring the Cl CH mixture to reflux. Then add dropwise ethanol until a N-soNH, clear solution results. Continue stirring and refluxing for N / 10 hours. Cool to room temperature and filter off the CH2 crystalline produce. Crystallize from ethanol. There are thus obtained 4.1 parts of N-3,4-dichlorobenzylsulf In a flask equipped with a stirrer and a condenser amide, melting point 106 to 107. attached to a bubble detector, dissolve 11.25 parts (0.05 In similar manner by separately replacing the 3,4-di mole) of 2,3,6-trichloro-N-methylbenzylamine and 7.2 chlorobenzylamine by an equivalent amount of each of: parts (0.075 mole) of sulfamide in 100 parts by volume 2,3,4,5-tetrachlorobenzylamine, of pyridine. Stir and reflux the resulting solution until 2,3,5,6-tetrachlorobenzylamine, and gassing is no longer detected in the bubble detector. Re 2,3,4,6-tetrachlorobenzylamine, move the solvent (pyridine) in vacuo on a rotary evapo rator. Crystallize the viscous residue from methanol each of the corresponding Compounds II is obtained. 5 5 Water. There are thus obtained 8.3 parts of N-methyl-N- 2,3,6-trichlorobenzylsulfamide, melting point 128.5 to EXAMPLE 8 131. N-2,5-dichloro-4-methylbenzylsulfanide In similar manner, by separately replacing the 2,3,6- trichloro-N-methylbenzylamine by an equivalent amount CH3- Cl 60 of each of: H N-methyl-N-2,6-dichlorobenzylamine Cl N-sonii, N-methyl-N-(2,4-dichloro-6-fluoro)-benzylamine CH N-methyl-N-2,4,6-trichlorobenzylamine, N-methyl-N-2,3,4,6-tetrachlorobenzylamine, In a flask equipped with a stirrer, condenser and 65 dropping funnel place 6.3 parts (0.033 mole) of 2,5-di N-methyl-2,3,5,6-tetrachlorobenzylamine, chloro-4-methylbenzylamine, 6.0 parts (0.05 mole) of N-methyl-N-(3-methyl-2,4,6-trichloro)-benzylamine and sulfamide and 75 parts by volume of water. Stir and N-methyl-N-(5-methoxy-2,3,6-trichloro)-benzylamine, bring the mixture to reflux. Then add dropwise ethanol each of the corresponding Compounds II is obtained. until a clear solution results. Continue stirring and re 70 fluxing for 10 hours. Cool to room temperature and filter EXAMPLE 11 off the crystalline product. Crystallize from ethanol. Preparation of starting materials-reductive amination There are thus obtained 4.7 parts of N-2,5-dichloro-4- of an aldehyde methylbenzylsulfamide, melting point 107 to 108. Charge a rocker-type autoclave with 53 parts (0.3 mole) In similar manner by separately replacing the 2,5-di of 2,4-dichlorobenzaldehyde, 150 parts by volume of iso 3,320,314 7 8 propanol, 25 parts of activated Raney nickel and a solu (B) Preparing primary amines-hydrolysis of the tion of 12.4 parts (0.4 mole) of methylamine in 125 parts benzyl hexamethylenetetramine salt.-Cool in an ice bath by volume of isopropanol. Flush the system with nitro a solution of 0.1 mole of crude 2,3,6-trichlorobenzyl bro gen, and then admit hydrogen thereto until the pressure mide in 120 parts by volume of chloroform. Admix the in the autoclave is 500 pounds per square inch (p.s.i.g.). thus-cooled solution with a saturated chloroform solu Activate the rocker and heat to 50. After hydrogen up tion of 15.4 parts (0.11 mole) of hexamethylenetetramine. take is complete (about one hour), cool resulting system Stir the obtained solution for 24 hours at room tempera to room temperature (20'). Filter the obtained product ture. through Celite. Concentrate the filtrate in a rotary evap Filter the resulting crystalline salt (24.3 parts, M.P. orator. Distil the residue to obtain 39.2 parts of N 10 168 to 176), and permit the filtrate to stand at room methyl-2,4-dichlorobenzylamine, boiling point (B.P.) 77 temperature for an additional 24 hours. Filter the addi to 80 at 1 mm. tional salt (5.4 parts, M.P. 173 to 180°) precipitated, and Although this example illustrates the use of specific combine with that previously obtained to give a yield of compounds by necessity, the only limitation with respect 29.7 parts of crude 2,3,6-trichlorobenzyl-hexamethylene to the preparation of starting materials within the contem 5 tetramine bromide. plation of this invention is that the R of Compound III Add the crude salt to 55 parts by volume of 6 N hydro is limited to ethyl, propyl and isopropyl, and the R6 of gen chloride, and steam distill until a total of 500 parts Compound V is limited to methyl. It is thus seen that, by volume of steam distillate (formaldehyde) is obtained. in place of the methylamine, there is similarly used ethyl Make the liquid in the steam distillate flask basic with 50 20 percent sodium hydroxide, and extract the resulting prod amine, propylamine or isopropylamine with correspond uct three times with diethylether. Dry the combined ether ing results. The 2,4-dichlorobenzaldehyde is likewise re layers with sodium sulfate. Filter the dried product and placed by an equivalent amount of any of the corre distil through a Claisen head. There are thus obtained sponding aldehyde precursors of Compounds III and V. 9.7 parts of 2,3,6-trichlorobenzylamine, B.P. 96° to 98° at 0.7 to 0.8 mm. EXAMPLE 12 25 Every primary amine within the scope of Compound Preparation of starting materials-lithium aluminum V is prepared according to this method. hydride reduction of a benzamide (C) Preparing secondary amines from the correspond Charge a flask (equipped with a stirrer, dropping fun ing benzyl bromide-Add a solution of 0.15 mole of crude nel, condenser and drying tube) with 10.4 parts (0.2 30 2,3,6-trichlorobenzyl bromide in 50 parts by volume of mole) of the cyclopropylamine and 200 parts by volume chloroform to a saturated chloroform solution of 0.5 of dry toluene. While stirring, add dropwise to the ob mole of methylamine. Reflux the resulting mixture for tained solution 11.5 parts by volume (0.1 mole) of benzoyl four hours, and then allow to stand over night at room chloride at a sufficient rate to raise the temperature to 45. temperature. Stir over night (about 17 hours). Filter off the obtained Filter of the precipitated crystalline methylamine hy crystalline cyclopropylamine hydrochloride. drobromide (16.8 parts, M.P. 253 to 255°). Concentrate Concentrate the filtrate in a rotary evaporator. Crystal the filtrate on a rotary evaporator, and distil the residue lize the resulting solid (10.7 parts) from methanol-water through a Claisen head. There are thus obtained 24.5 to obtain 9.5 parts of N-cyclopropylbenzamide, M.P. 95 parts of N-methyl-N-2,3,6-trichlorobenzylamine, B.P.97° to 97. 40 s 0.07 mm., that solidify to a material of M.P. 51° to Place in a flask equipped with a stirrer, Soxhlet extrac tion apparatus and a gas inlet-exit system 500 parts by The preceding method is suitable for the preparation of volume of absolute diethylether and 2.7 parts (0.07 mole) all Compounds III and every Compound V wherein R6 is of lithium aluminum hydride. Place 9.5 parts (0.07 methyl. mole) of N-cyclopropylbenzamide in a Soxhlet extrac It is thought that the invention and its advantages will tion cup, and insert same in the extractor. Blanket the be understood from the foregoing description. It is ap system with nitrogen, agitate and bring to reflux. Reflux parent that various changes may be made in the structures until all of the amide has been extracted from the cup. of Compounds I and II without departing from the spirit Thereafter, allow the resulting mixture to cool to room and scope of the invention or sacrificing its material ad temperature. 50 Yantages. The examples merely provide illustrative em Admix with the thus-cooled mixture 5.7 parts by volume bodiments. It is essential for all compounds of this in of ethyl acetate to react with excess hydride. Then add vention that there be at least one chlorine substituent bond thereto 8.1 parts by volume of 2 N sodium hydroxide to ed to a ring carbon atom of the aromatic nucleus. In ad decompose the formed hydride complex. Filter off the dition Compounds I must have at least one ortho-unsub resultant salts and wash same with diethylether. Com 55 stituted position on the aromatic nucleus, and Compound bine the ether wash and the filtrate on a rotary evaporator. II must have at least one unsubstituted position on the Distil the resulting residue (8.8 parts) through a Claisen aromatic nucleus. head. There are thus obtained 5.2 parts of N-cyclopropyl What is claimed is: benzylamine, B.P. 50 to 51 at 0.3 mm. 1. A compound of the formula There are no limitations to this illustrative example 60 Ri in so far as the preparation of any compounds within the scope of Compounds III and V is concerned. CE R2- N-so-NH, EXAMPLE 13 R3 H. R. Preparation of starting materials 65 (A) Preparing the benzyl bromide.-Place in a fiask equipped with a stirrer, dropping funnel and a condenser wherein (equipped with a bubble detector) 0.1 mole of 2,3,6-tri R is cyclopropyl; and chlorotoluene. Stir and heat to about 120°. Then add 70 each of dropwise thereto 0.105 mole of bromine at a rate suffi cient to evolve hydrogen bromide vigorously. Cool the re R", R, R, and R is a member selected from the group Sulting product to room temperature after the addition is consisting of a hydrogen atom, lower alkyl, lower complete. Dissolve the obtained crude 2,3,6-trichloro alkoxy, fluoro and chloro; at least one of R1, R2, R3 benzyl bromide in 120 parts by volume of chloroform. 75 and R4 being chloro. 3,320,314 9 10 2. A compound of the formula wherein

. CH R is 6-methallyl; and R2- M S-so-sh, each of 5 R1, R2, R3, and R4 is a member selected from the group R -H. R. consisting of a hydrogen atom, lower alkyl, lower alkoxy, fluoro and chloro; at least one of R, R, R8 R4 and R4 being chloro. wherein 10 6. A compound of the formula R is allyl; and each of R1 R1, R2, R3, and R4 is a member selected from the group CH, consisting of a hydrogen atom, lower alkyl, lower 15 R2- N NH alkoxy, fluoro and chloro; at least one of R, R, R8 so- 2 and R4 being chloro. R3- -H 3. N-allyl-N-3,4-dichlorobenzylsulfamide. 4. A compound of the formula R4 R 20

R2 CR N-so-NH. wherein R.3-l. J.-H. R. 2 R is g,8-dimethallyl; and k each of wherein R, R2, R3, and R4 is a member selected from the group Ri hallwl; and consisting of a hydrogen atom, lower alkyl, lower is a-methallyl; an alkoxy, fluoro and chloro; at least one of R, R2, R: each of and R being chloro. R1, R2, R3, and R4 is a member selected from the group consisting of a hydrogen atom, lower alkyl, lower References Cited by the Ex e alkoxy, fluoro and chloro; at least one of R, R, R UNITED STATES PATENTS and R4 being chloro. 35 3,143,549 8/1964 Lafferty ------260-340.5 X 5. A compound of the formula FOREIGN PATENTS R 947,554 8/1956 Germany. et 789,273 1/1958 Great Britain. R2- N-SO-NH 40 WALTER A. MODANCE, Primary Examiner. JOHN D. RANDOLPH, Examiner. 4. HARRY I. MOATZ, Assistant Examiner.