The Preparation of Phenylimido Phosgene And the Chlorination of Formanilide

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It is also possible that phenylisocyanide, formed by dehydration of an enolic form of formanilide, adds chlorine to give the observed products. 13 Experimental Preparation of Phenyl Mustard Oil. Fifteen moles of dil. Sulfuric acid, 3689 g. , was mixed with 5 moles, 1140 g. , of thiocarbanilide and the mixture refluxed for 6 hours. The dilute acid was prepared by adding 5 parts of water by volume to 2 parts of 1. 84 sulfuric acid; the temperature of refluxing ranged from 140-160. The refluxed mi
...xture was distilled with steam, and the mustard oil separated, dried with calcium chloride, distilled at ordinary pressure, and collected at 215-221. The yields averaged 70%, based upon the equation, C 6 H6NHCSNHC 6 H 6 > CeHaNCS + CeH^NHz. In one run, steam and hydrogen sulfide were passed through the residue from the first steam distillation for an hour, with a view to breaking up the triphenyl-guanidine by-product into aniline and phenyl mustard oil, but no product was formed. After neutralizing the residue, 83% of the aniline was recovered in the usual manner.

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