Verfahren zur Herstellung von Mercaptomethylnaphthochinonderivaten

摘要

The invention relates to compounds of the formula in which X is an alkyl, aralkyl or aryl radical, which may be substituted by a group -N(Alkyl)2, COOH, COOAlkyl or C(O)N(Alkyl)2, or is a group -C(S)OAlkyl, -C(S)NH2, -C(S)NHAlkyl, -C(S)N(Alkyl)2, -C(S)N Alkylene (the nitrogen atom and the alkylene group forming a heterocyclic ring); -P(S)(O Alkyl)2, -C(NH)NH2, -C(S) Alkyl, -C(S)Aryl, -C(O)Alkyl or C(O)Aryl, R11 is a hydrogen atom or a methyl radical, R1 is a hydrogen or halogen atom or an alkyl, nitro or sulphonic acid group, R is a halogen atom, a methyl or ethyl group, an aryl group, or a group -C(R11)HSX, and n is 1-4. The compounds may be prepared by condensing an appropriately substituted naphthoquinone derivative carrying a 2-halogenmethyl or 2-a -halogen-ethyl group with an appropriate compound containing at least one mercapto group. The reaction may be effected at atmospheric temperature in a solvent, e.g. methanol or ethanol. In the examples, (1) the compound is prepared from 2-chloromethyl-3-methyl-1, 4-naphthoquinone and potassium ethyl xanthate; (2) the compound is prepared from 2, 3-bis-chloromethyl-1, 4-naphthoquinone and potassium ethyl xanthate; (3) the compound is prepared from 2-chloromethyl-3-methyl-1, 4-naphthoquinone and potassium O,O-diethylthionothiolphosphate; (4) the compound is prepared from 2-chloromethyl-3-methyl-1,4-naphthoquinone and potassium O,O-diethylthionothiolphosphate; (5) the compound is prepared from 2-chloromethyl-3-methyl-1,4- naphthoquinone and thiourea; (6) the compound is prepared from 2,3-bis-chloromethyl-1,4- naphthoquinone and thiourea; (7) the compound is prepared from 2-chloromethyl-3-methyl-1,4-naphthoquinone and potassium pentamethylene dithiocarbomate; (8) the compound is prepared from 2,3-bis-chloromethyl-1,4-naphthoquinone and sodium pentamethylene dithiocarbamate. Reference is made also to the condensation of the naphthoquinone derivatives with alkyl mercaptans, thiophenols, benzyl mercaptan, thioglycollic acid and sodium methyl- or dimethyl -dithiocarbamate. 2 - Chloromethyl - 3 -chloro-1,4- naphthoquinone is an additional specified starting material.