GB732386A - Improvements in or relating to manufacture of n-trichloromethylthioimides - Google Patents

Abstract

A process for the preparation of N-trichloromethyl derivatives represented by either of the general formul <FORM:0732386/IV (b)/1> or <FORM:0732386/IV (b)/2> wherein R is an organic radical or nucleus, and X and Y are >CO and/or >SO2 or wherein X is a methylene group or an alkyl or cycloalkyl-substituted derivative thereof and Y is =SO2 or =CO, and wherein X1 is RCO or RSO2 and Y1 is RCO or RSO2 or R or H, of the type wherein an imide, sulphimide, amide or sulphonamide or a metal derivative thereof is reacted with admixed perchloromethyl mercaptan, is characterized in that the said imide, sulphimide, amide or sulphonamide is dissolved in an aqueous solution of a basic alkali metal compound, and the resulting solution is reacted with admixed perchloromethyl mercaptan in the presence of a water-immiscible solvent for perchloromethyl mercaptan which is a non-solvent for the said N-trichloromethyl derivatives. The solvents preferably have a boiling point between 50 DEG and 150 DEG C. Specified are C5 to C9 saturated hydrocarbons (aliphatic or naphthenic), e.g. heptane, hexane, cyclohexane, virgin naphtha, ethers of boiling point 80 DEG to 120 DEG C., e.g. dipropyl and butyl ethyl ethers, or halogenated hydrocarbons, e.g. ethylene di-and trichlorides, b -trichlorethane and 1,2-dichloropropane. In examples (1) to (3) N-trichloromethylthiotetrahydrophthalimide is prepared by dissolving tetrahydrophthalimide in aqueous sodium hydroxide solution and reacting the product with perchloromethyl mercaptan dissolved in heptane. The recovered heptane is analysed. A control experiment without heptane is also performed. In a generally similar manner there are prepared (4) N-trichloromethylthio - o - benzoic sulphimide; (5) 1-nitro - 3 - trichloromethylthio - 5,5 - dimethylhydantoin; (6) N-trichlormethylthio-N-phenylbenzenesulphonamide. Other compounds of which the N-trichloromethylthio derivatives can be prepared are phthalimide, succinimide, endomethylenetetrahydrophthalimide, chlorinated tetrahydrophthalimide, 2,4 - dioxothiazolidine, 5,5 - dimethyloxazolidine - 2,4 - dione, 5-methyl - 5 - ethyloxazolidine - 2,4 - dione, 5,5-pentamethylene - oxazolidine - 2,4 - dione, 5-methyl - 5 - phenyl - oxazolidine - 2,4 - dione, 5 - methyl - 5 - isobutyl - oxazolidine - 2,4-dione, 5,5 - dimethylhydantoin, 1 - acetyl-5,5 - dimethylhydantoin, 5 - methyl - 5 - isobutylhydantoin, iso - octyloxazolidine - 2,4-dione, 5 - methyl - 5 - cyclopropyl - oxazolidine-2,4-dione, and N-butyl-benzenesulphonamide. Specifications 666,636 and 716,553 are referred to.