Process for the preparation of Chloroalkyl-S-Alkyl-and Aryl-Mono- or Di-Thiolphosphoric Acid Diester and Ester Amide Chlorides

摘要

1,158,709. Chloroalkyl-S-alkyl- (or aryl) mono- (or di-) thiolphosphoric acid diester or ester amide chlorides. FARBENFABRIKEN BAYER A.G. 17 Jan., 1968 [13 Feb., 1967], No. 2521/68. Heading C2C. Chloroalkyl - S - alkyl- or -aryl - mono- or di-thiolphosphoric acid diester or ester amide chlorides are obtained by reacting a 2-chlorophospholane or -phosphorinane derivative of the general formula with an aliphatic or aromatic sulphenic acid chloride of the formula R 7 -S-Cl, in which R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are hydrogen atoms, alkyl, alkoxyalkyl or haloalkyl radicals, R, is an alkyl, alkenyl, or aryl radical (which may be substituted), X is an oxygen or sulphur atom or a N-alkyl- or N-aryl-amino group, n is 0 or 1, and if n is 1, then the radicals R 3 and R 4 together with the 5-carbon atom may also form a further heterocylic ring of the structure R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are preferably hydrogen atoms or alkyl radicals with 1 to 4 carbon atoms, which may be substituted by halogen or lower C 1 to C 6 alkoxy groups such as methyl, chloromethyl or methoxymethyl radicals. A large number of possible substituents for the group R 7 are listed, and in the examples the following sulphenic acid chlorides are used; methyl-, 4-tolyl-, 4-chlorophenyl-, 2-nitrophenyl- and phenyl-, and also 2-chlorosulphenylisobutyraldehyde. The process may be carried out in the presence of solvents or diluents at -20‹ to +50‹ C., preferably at -10‹ to +30‹ C., and the molar ratio of the 2-chlorophospholane or -phosphorinane to the sulphenic acid chloride is preferably 1 : 1.