N-CHLOROMETHYL-N-PHENYLCARBAMOYL CHLORIDE

There are phosgene route and non-phosgene route for the synthesis of chloride. The phosgene route is the reaction of N-methylaniline and phosgene to generate N-methyl-N-phenylcarbamoyl chloride, which is then further chlorinated on the N-methyl group to obtain the desired chloride. The carbon tetrachloride is pumped into the photochemical reaction kettle, and N-methylaniline and carbon tetrachloride are pumped into the N-methylaniline dropping tank for later use. When heated to 40°C, phosgene was continuously introduced, and N-methylaniline carbon tetrachloride solution was added dropwise at the same time, and the dropping rate was limited to no precipitation. After the dripping, stop phosgene, cool to room temperature, vent the excess phosgene with nitrogen, and obtain N-methyl-N-phenylcarbamoyl chloride carbon tetrachloride solution. Add this solution to the chlorination reaction kettle, irradiate it with ultraviolet light at 20°C for 0.5h, and then pass in chlorine gas. As the reaction exotherms, the temperature gradually rises and reacts for about 2 to 4 hours. When the reaction solution begins to cool down, cool it to At 20°C, continue to pass in chlorine gas under light, and the chlorination depth is monitored by gas chromatography. After the reaction is completed, nitrogen is blown out to drive out hydrogen chloride and excess chlorine, the reaction solution is decompressed and desolventized, and carbon tetrachloride is recovered to obtain the finished product chloride. The non-phosgene route N-methylaniline first reacts with formic acid to generate N-methylanilide, and then in the presence of benzoyl peroxide, the methyl and aldehyde groups are simultaneously chlorinated to obtain the desired chloride. A certain amount of N-methylaniline and formic acid are added to the reactor, heated to make the reaction liquid in a slightly boiling state, and the distillate is maintained to be evaporated. After about 4.5h, the internal temperature of the reaction solution gradually increased to 170°C, and no distillate was evaporated. At this time, the reaction was stopped, cooled, and distilled under reduced pressure to obtain anilide. Then put N-methylformanilide, carbon tetrachloride and benzoyl perchloride into the chlorination reactor, pre-gas chlorine, raise the temperature to 80℃, keep the chlorine gas flow rate at 0.17g/min, gas chromatography Follow up analysis and determine the end of the reaction. After the chlorine gas is stopped, nitrogen gas is changed to drive off the HCl, and the carbon tetrachloride is recovered, and then distilled under reduced pressure and recrystallized to obtain the desired chloride.

N-chloromethyl-N-phenylcarbamoyl chloride, referred to as chloride, is an intermediate of the insecticide thiazinone.

Molecular Weight:204.05
XLogP3:3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:202.9904692
Monoisotopic Mass:202.9904692
Topological Polar Surface Area:20.3
Heavy Atom Count:12
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes