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United States Patent Office Patented Feb 3,639,471 United States Patent Office Patented Feb. 1, 1972 2 In this reaction (i), therefore, an intramolecular 3,639,471 splitting off occurs of hydrogen chloride from the car PROCESS FOR THE PREPARATION OF SULFEN bamic acid chloride molecule. YLATED CARBAMIC ACD FLUOR DES Erich Klauke, Odenthal-Hahnenberg, and Engelbert It has not hitherto been known, or successfully carried Kuhle, Bergedorf, Gladbach, Germany, assignors to out, that in monosubstituted carbamic acid chlorides the Farbenfabriken Bayer Aktiengesellschaft, Leverkusen, hydrogen atom on the nitrogen atom can be reacted with Germany acid chlorides, that is, that the hydrogen atom can be re No Drawing. Filled July 3, 1968, Ser. No. 742,176 placed by an acid radical. In this second case, an inter Claims priority, application Germany, July 5, 1967, molecular, rather than an intramolecular, splitting off of F 52,861 0. hydrogen chloride would be necessary. Int. C. C07c51/58, 101/10, 125/00 'If monosubstituted carbamic acid chlorides are reacted U.S. C. 260-544 C 20 Claims with acid-binding agents, such as triethylamine, and sul fenic acid chlorides, such as trichloromethyl-sulfenyl chloride, there is also obtained the appropriate isocyanate, ABSTRACT OF THE DISCLOSURE 5 since the trichloromethyl-sulfenyl chloride does not react. Reacting N-mono-(substituted- and unsubstituted-ali Thus, there occurs here again an intramolecular, in phatic, e.g. lower alkyl, -cycloaliphatic, e.g. C5-6 cyclo stead of an intermolecular, splitting off of hydrogen alkyl; and -aromatic, e.g. phenyl and halo-, nitro-, lower chloride. alkyl-, lower alkoxy-, lower alkylmercapto- and/or tri The second case reaction can be represented for ex fluoromethyl-phenyl)-substituted carbamic acid fluoride 20 ample by the following formula scheme: with (substituted- and unsubstituted-alkyl, e.g. haloalkyl; and -aryl, e.g. halo-, alkyl- and/or nitro-aryl, especially -phenyl)-sulfenic acid chloride or sulfur dichloride or di CO-Cl sulfur dichloride, in the presence of a tertiary amine as (ii) -N -- (CF3)3N -- ClS-CCl3 -> acid binding agent, e.g. at a temperature of about 0-100 25 H C., optionally in the presence of an inert organic solvent, (A) using about one mol of the carbamic acid fluoride per mol of said sulfenic acid chloride or at least two mols per mol of the sulfur dichloride or disulfur dichloride, to form the corresponding aforesaid N-(substituted- and 30 (B) (IIbb) unsubstituted-aliphatic, -cycloaliphatic and -aromatic)- N-(substituted- and unsubstituted-alkyl and -aryl)-sul If monosubstituted carbamic acid fluorides are reacted fenyl-carbamic acid fluoride and bis(N-substituted- and with an acid-binding agent, such as trimethylamine, and unsubstituted-aliphatic, -cycloaliphatic or -aromatic-N- a carboxylic acid chloride, such as acetic acid chloride, fluorocarbonyl)-amino-sulfide and -disulfide, which are the appropriate isocyanate in this third case is again ob particularly new compounds which possess arthropo tained. Here, too, there occurs merely an intramolecular dicidal, e.g. insecticidal and acaricidal, as well as fungi splitting off of hydrogen fluoride, but no intermolecular cidal properties, and which may be used as intermediates splitting off of hydrogen chloride. in organic synthesis. The course of this third case reaction can be represented 40 for example by the following formula scheme: The present invention relates to and has for its objects the provision for particular new methods of producing sulfenylated carbamic acid fluorides, and more particularly (iii) { X-NC cof -- (CBI)3N -- CH-CO-Cl -> N-(lower alkyl, C5-6 cycloalkyl, phenyl and halo- and 45 lower alkyl-substituted phenyl)-N-(halolower alkyl and H phenyl)-sulfenyl]-carbamic acid fluorides and bis-(N- (Iaa) (C) lower alkyl, C.s 6 cycloalkyl, phenyl and halo- and lower alkyl - substituted phenyl-N-fluorocarbonyl)-amino-sul { X-N=C=o -- (CH3) N.HCl -- CH-COF fides and -disulfides, which are particularly new com 50 pounds which possess arthropodicidal and fungicidal (B) (D) properties and which may be used as intermediates in organic synthesis, e.g. in a simple single step reaction, It has now been found, in accordance with the present using readily available starting materials whereby to at invention, that sulfenylated carbamic acid fluorides, i.e. tain outstanding yields, with other and further objects 55 N-(lower alkyl, C5-6 cycloalkyl, phenyl and halo- and of the invention becoming apparent from a study of the lower alkyl- substituted phenyl)-N-(halolower alkyl and within specification and accompanying examples. phenyl)-sulfenyl-carbamic acid fluorides and bis-(N- It is known that monosubstituted carbamic acid lower alkyl, C5-6 cycloalkyl, phenyl and halo- and lower chlorides can be converted smoothly into isocyanates with alkyl- substituted phenyl-N-fluorocarbonyl)-amino-sul fides and -disulfides, which are particularly new com acid-binding agents such as trimethyl amine (cf. Ann. 60 pounds which possess arthropodicidal, i.e. insecticidal and 562, 78 (1949). The course of the reaction can be acaricidal, as well as fungicidal properties, and which may represented for example by the following formula Scheme: be used as intermediates in organic synthesis, having the CO-C formula 65 co F (i) () (, -- (CH3)3N --> R-N (I) S-R2 (A) in which R1 is selected from the group consisting of lower ()-N=C=o -- (CH3)3N.HCl 70 alkyl, cycloalkyl having 5-6 ring carbon atoms, phenyl, (B) and substituted phenyl which is substituted with substitu 3,639,471 3 4 ents selected from the group consisting of lower alkyl and The starting materials are clearly characterized by the 1-3 halo, and Ra is selected from the group consisting above-mentioned Formulae IIa and IIb and even typify of halo lower alkyl, phenyl, the radical the analogous use of sulfur dichloride and disulfur di COF chloride. The carbamic acid fluorides (IIa) mentioned as start ing materials are already known (compare Soc. 1945, 864). As examples, there may be mentioned: methyl, and the radical butyl, isopropyl, cyclohexyl, phenyl, 4-chlorophenyl, 3 methylphenyl, 3-nitro-phenyl, 4-ethoxy-3-chloro-phenyl, O 3-trifluoromethyl-phenyl, 4-methylmercapto-phenyl, naph -S-N (ii) N thyl isocyanate, and the like. R The sulfenic acid chlorides to be used are also known in which the last-mentioned two R1 symbols are the same As examples there may be mentioned: sulfur dichloride, as defined above, can be obtained simply, that is in a disulfur dichloride, methyl-sulfenylchloride, perchloro one-step reaction, in high purity and with outstanding methylmercaptan, fluoro-dichloro-methyl-sulfenylchloride, yields, by the process which comprises reacting mono phenyl-sulfenylchloride, 4-chlorophenyl-sulfenylchloride, substituted carbamic acid fluorides, i.e. N-mono-(lower 4-tolylsulfenylchloride, 2-nitrophenyl-sulfenylchloride, and alkyl, C5-6 cycloalkyl, phenyl and halo- and lower alkyl the like. substituted phenyl)-substituted carbamic acid fluorides The reaction is expediently, though optionally, carried having the general formula 20 out in the presence of an organic solvent. COF As solvents (which term includes a mere diluent) which / may optionally be used in accordance with the process of R-N (IIa) the present invention, all inert organic solvents and mix H tures thereof are suitable. Preferred solvents include hy drocarbons, especially aliphatic and aromatic hydrocar in which R1 is the same as defined above, with a member bons and mixtures thereof, such as petroleum ether frac selected from the group consisting of sulfenic acid chlo tions, benzene, toluenes, and/or xylenes; chlorinated hy rides having the formula drocarbons, especially chlorinated aliphatic and chlori R2a-S-Cl (IIb) nated aromatic hydrocarbons and mixtures thereof, such in which R2 is halo lower alkyl or phenyl, sulfur dichlo 30 as carbon tetrachloride, methylene chloride, 1,1,2,2-tetra ride and disulfur dichloride, in the presence of a tertiary chloroethane, chlorobenzene, o-dichlorobenzene and/or a amine as acid-binding agent, for example at a temperature chloronaphthalene; ethers, especially aliphatic ethers, par substantially between about 0-100° C. Thus, in the last ticularly lower alkyl ethers, such as diethyl ether, cyclo mentioned formula R2a actually contemplates not only aliphatic ethers, such as dioxan; ketones especially ali halo lower alkyl and phenyl radicals corresponding to phatic ketones, particularly lower alkyl ketones, such as R of Formula I but also a chloro or chlorothio (i.e. methyl-isobutyl ketone; and esters, especially aliphatic Cl-S-) group, whereupon in the latter two cases two ether-aliphatic carboxylic acid esters including low mols of the mono-substituted carbamic acid fluoride should er alkoxy lower alkyl esters of lower alkanoic acids, such be used rather than one mol with the C1-S-Cl or as glycolmonomethyl ether acetate, i.e. methylglycol ace Cl-S-S-Cl reactant to obtain corresponding formula 40 tate, and glycolmonoethyl ether acetate; mixtures of the (I) compounds having the radicals foregoing; and the like. As acid-binding agents, all tertiary organic amines cus COF cof tomarily used for this purpose are suitable. These include -N and -S-N N N tertiary aliphatic, aromatic, mixed aliphatic-aromatic, and R R 45 heterocyclic amines such as trilower alkyl amines, tri for R2. phenyl amine, mixed lower alkyl and phenyl amines, tri The reaction may optionally take place in the presence benzyl amine, mixed lower alkyl, phenyl and benzyl of an inert organic solvent or diluent. amines, 5-membered heterocyclic amines, etc., for exam Advantageously, as aforesaid, by means of the instant ple trimethyl amine, triethyl amine, pyridine and dimethyl process the particular new carbamic acid fluorides of the 50 benzyl amine. present invention may be obtained in one step and with The reaction temperatures can be varied within a fairly high yields. wide range. In general, temperatures are substantially be It is very surprising that in accordance with the pro tween about 0 to 100 C., preferably from about 10 to duction process of the present invention the hydrogen 40° C.
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