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United States Patent Office Patented May 7, 1963 1 3,088,977 United States Patent Office Patented May 7, 1963 1. 2 the solvent employed. The reaction is ordinarily com plete in a few hours. The inorganic salts are then fil HEXACHELOROTETRAHYDROMETHANOINDENE3,938,977 tered off, and the product is isolated by distilling off the AMINE COMPOUNDS solvent in vacuo. The residue can be used directly in the Edward Segel, Chicago, Ill., assignor to Welsicol Chemical next step in the synthesis, or it can be purified by re Corporation, Chicago, Ill., a corporation of Illinois s crystallization from a suitable solvent such as pentane. No Drawing. Filed May 18, 1959, Ser. No. 813,661 This intermediate isothiocyanate is then hydrolyzed in 6 Claims. (Cl. 260-563) aqueous medium in the presence of a few percent by Weight of a strong mineral acid such as hydrochloric acid. This invention relates to new chemical compositions of Although a solvent is not absolutely essential, the hy matter. More specifically, this invention relates to new O drolysis can be facilitated by the use of a relatively inert chemical compounds of the formula solvent or diluent such as dioxane. Reaction tempera i tures between about normal room temperature and the C H reflux temperature of the reaction mixture are satisfac 5 tory. When the hydrolysis is complete, the liquid com ponents are distilled off in vacuo. The residue consists primarily of the acid salt of the desired primary amine. The free amine can be obtained by making the residue basic with an aqueous solution of base such as sodium 20 or potassium hydroxide and then extracting the basic d R-N-R, mixture with a water-immiscible organic solvent such as wherein R and R are selected from the group consisting ether. The ether solution is then dried and filtered, and of hydrogen and the radicals -(CH2)CH3 the ether is distilled off. While the residue of the de sired primary amine obtained in this manner is often sufficiently pure for pesticidal use as such, if desired it -(CH2)Y, and -(CH2)2SH, n is a whole number from can be purified, for example, by recrystallization from a O to 6, x is a whole number from 2 to 7, z is a whole suitable solvent such as pentane. number from 1 to 7, and Y is selected from the group When one of R or R is hydrogen and the other is one consisting of chlorine and bromine. These compounds of the radicals listed above, the new compounds of this are useful as pesticides, particularly as fungicides and 30 invention are secondary amines. These amines can be nematocides. prepared by treating Compound I with the appropriate The new compounds of this invention can be prepared primary amines HN (CH2)CH, HN (CH)OH, or readily from the compound 1-bromo-4,5,6,7,8,8-hexa H2NCCHg),SH, where n, x, and g are as previously de chloro-3a,4,7,7a-tetrahydro-4,7-methanoindene, which will fined. While equimolar proportions of the reactants can be referred to as Compound I for brevity. Compound I 35 be used, it is preferable to use an excess of up to about itself can be obtained by the bromination of 4,5,6,7,8,8- one mole of the amine reactant. In some cases, the hexachloro-3a,4,7,7a-tetrahydro - 4.7-methanoindene, the amine reactant is a liquid at normal room temperature, Diels-Alder adduct of hexachlorocyclopentadiene and cy so that no other solvents or diluents need be used. Sim clopentadiene as described, for example, by Riem ilarly, some of the amine reactants are supplied commer schneider, Monatsh. 83, 802(1952). The bromination is O cially as aqueous solutions which can be used directly for preferably carried out in the presence of a small quantity reaction with Compound I in a two-phase system, which (about 0.001 to 0.01 mole per mole of adduct) of an should be stirred thoroughly during the reaction. How organic peroxide such as benzoyl peroxide, lauryl per ever, other inert solvents or diluents can be used to fa oxide, or ascaridol. One mole of bromine or preferably (cilitate the reaction. The reaction temperature is not a slight excess should be used for each mole of adduct. 45 critical, but temperatures in the range from about nor The bromine is added portionwise to the adduct, which mal room temperature to about the reflux temperature of is suitably dissolved in an inert solvent such as carbon the reaction mixture are preferred. The reactions can tetrachloride, chloroform, carbon disulfide, tetrachloro be carried out satisfactorily at normal atmospheric pres ethylene, or the like. Reaction temperatures between sure, but Super- or subatmospheric pressures can be used about normal room temperature and about 120° C. are 50 suitable. After all the bromine has been added, the if desired. The length of time required for the reaction product can be isolated by distilling off the solvent and depends on many factors and will vary from a few any excess bromine in vacuo. The yields of Compound minutes to a matter of hours. Similarly, the reaction I are nearly quantitative. While the Compound I ob mixture is worked up in a manner suitable to the phys tained in this manner is often sufficiently pure to be used 55 ical properties of the reactants and the particular prod directly as a starting material in the preparation of the uct, Generally, however, if the reaction has been carried compounds of this invention, it can be purified, as by re out in an organic solvent, the hydrobromide of the pri crystallization from a suitable solvent such as hexane or, mary amine used as starting material will have precipi pentane. tated out and can be filtered off. The solvent is then dis When both R and R1 are hydrogen, the new com 60 tilled off from the filtrate in vacuo to leave a residue of pound of this invention is the primary amine 1-amino the desired secondary amine and any unreacted Com 4,5,6,7,8,8-hexachloro - 3a,4,7,7a - tetrahydro-4,7-methan pound I. This residue is treated with an aqueous solu oindene. This compound can be obtained, for example, tion of a mineral acid such as hydrochloric acid and by treating Compound I with a thiocyanate such as so filtered. The filtrate is then made strongly basic with dium or potassium thiocyanate and hydrolyzing the re-f 65 an aqueous solution of a base such as sodium or potas sulting isothiocyanate. The first reaction is preferably sium hydroxide, and the mixture is extracted thoroughly carried out with a slight excess of thiocyanate over the theoretically required one mole for each mole of Com with a water-immiscible organic solvent such as ether. pound I. A relatively inert solvent or diluent such as The ether solution is then dried and filtered, and the acetone is used to facilitate the reaction, which can be 70 ether is distilled off. While the residue is often suffi carried out satisfactorily at temperatures between about ciently pure for pesticidal use as such, the desired second normal room temperature and the reflux temperature of ary amine can be isolated in pure form by fractional 3,088,977 3. 4. distillation, recrystallization, or other techniques known monium salts can be formed by the alkylation of the to those skilled in the art. amines of this invention with such alkylating agents as Secondary amines according to this invention in which alkyl halides, sulfates, and sulfonates. The salts of the one of R or R1 is a radical -(CH2)CH3 are prepared tertiary amines ordinarily form readily from the amine by the reaction of Compound I with methylamine, ethyl and the alkylating agent when they are allowed to stand anine, propylamine, butylamine, amylamine, hexylamine, at room temperature in a nonpolar solvent such as ben or heptylamine. Amine products in which one of R or Zene or xylene. Formation of the quaternary salts from R1 is a radical -(CH)OH are prepared from Com the primary amine or secondary amines requires the pres pound I and 2-aminoethanol, 3-aminopropanol, 4-amino ence of a base such as sodium carbonate. The quater butanol, 5-aminopentanol, 6-aminohexanol, or 7-amino nary salts are ordinarily very insoluble in nonpolar sol heptanol. Similarly, amine products which contain the vents and precipitate out as they form; hence they can radical -(CH2)SH are prepared from Compound I and simply be filtered off, washed, and dried. Typical ex such amines as aminomethanethiol, 2-aminoethanethiol, amples of quaternary ammonium salts are those formed 7-aminoheptanethiol, and the like. by the addition of the amines of this invention, especial Secondary amines according to this invention in which 5 ly the tertiary amines, to alkyl halides such as methyl R or R1 is a radical -(CH2)Y can be obtained by iodide, methyl bromide, ethyl chloride, ethyl bromide, treating the secondary amines containing a radical ethyl iodide, propyl bromide, isopropyl iodide, butyl -(CH2)OH with a halogenating agent such as thionyl chloride, butyl bromide, isobutyl iodide, and the like. chloride or thionyl bromide. It is preferred to use a The manner in which the new compounds of this in slight molar excess of the halogenating agent, which is 20 added portionwise to the hydroxyamine, which can be examples.vention can be prepared is illustrated in the following mixed with a suitable solvent or diluent. In many cases EXAMPLE 1. the reaction is exothermic, and no external heat need be applied. In general, reaction temperatures between about Preparation of 1-Bromo-4,5,6,7,8,8-Hexachloro normal room temperature and the reflux temperature of 25 3a,4,7,7a-Tetrahydro-4,7-Methanoindene the reaction mixture are satisfactory.
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