Production of nu-substituted carbamyl chlorides

The invention comprises N-substituted carbamyl chlorides having the formula or wherein R1 is alkyl or phenyl, R2 is hydrogen or alkyl, R3 is hydrogen, alkyl or phenyl, and R4 is alkylene. The invention further comprises the preparation of these and other N-substituted carbamyl chlorides, wherein phosgene is reacted with an aliphatic or araliphatic acid amide containing one or more acylamino groups, in the stable or keto form of which only one hydrogen atom is bound to the nitrogen atom of the or each acylamino group present and at least one hydrogen atom is bound to the carbon atom next to the carbon atom of the or each acylamino group present, the said acid amide being used (a) as such and while ensuring that at all or substantially at all times during the reaction there is an excess of the phosgene over the stoichiometric amount (i.e., more than 2 molar proportions of phosgene per said acylamino group), or (b) in the form of the hydrochloric acid salt. When the acid amide is used as such, the necessary excess of phosgene is ensured by slowly adding the acid amide to the total required quantity of phosgene. When the acid amide is used in the form of the hydrogen chloride salt, the phosgene may be added to the salt. Solvents such as hydrocarbons and halogenated hydrocarbons may be used in the reaction. The reaction may be carried out at atmospheric or superatmospheric pressure, preferably between 10 and 25 atmospheres. Preferably, the reaction is initiated at a temperature between -5 DEG and +45 DEG C., and after a short period the temperature is raised to between 45 DEG and 120 DEG C. The examples illustrate the preparation of N-n-propyl-N-(1-chloro-1-propenyl) - carbamyl chloride, N - n - propyl - N - (1 - chloro - 1 - octadecenyl) - carbamyl chloride, N - n - propyl - N - (1 - chloro - 1 - isobutenyl) - carbamyl chloride, N - phenyl - N - (1 - chloro - 1 - propenyl) - carbamyl chloride, N - methyl - N - (1 - chloro - phenyl - ethenyl) - carbamyl chloride and N,N1 - bis - (1 - chloroethenyl) - hexamethylene - 1,6 - dicarbamyl chloride. The N-substituted carbamyl chlorides can serve as intermediates in the preparation of urethanes. Specifications 901,169 and 901,170 are referred to.