Process for preparing N-alkoxycarbonyl-N-alkylcyanamide

Abstract

Quaternary ammonium salts act as phase transfer catalysts when present in reactions of alkoxycarbonylcyanamide with di-C 1-3 alkyl sulfate.

What is claimed is: 
     
       1. In a process for preparing N-.[.ethoxycarbonyl.]..Iadd.alkoxycarbonyl.Iaddend.-N-alkylcyanamides of the formula ##STR7## wherein R is alkyl of 1-3 carbon atoms and R' is alkyl of 1-3 carbon atoms by mixing an aqueous solution of an alkali or alkaline earth metal salt of N-alkoxycarbonylcyanamide with a di-C 1-3  alkyl sulfate, the improvement which comprises mixing said aqueous solution with said di-C 1-3  alkyl sulfate in the presence of at least about 0.1 mole % of quaternary hydrocarbyl ammonium ions per mole of N-alkoxycarbonylcyanamide, the hydrocarbyl moieties being selected from the group consisting of alkyl, aryl, alkaryl and aralkyl groups having a total carbon content of from 7 to 60 carbon atoms. 
     
     
       2. The process of claim 1 in which the hydrocarbyl moieties are selected from the group consisting of alkyl, aryl, alkaryl and aralkyl groups having a total carbon content of 10 to 50 carbon atoms. 
     
     
       3. The process of claim 1 in which the hydrocarbyl moieties are selected from the group consisting of alkyl, aryl, alkaryl and aralkyl groups having a total carbon content of 12 to 20 carbon atoms. 
     
     
       4. The process of claim 1 in which the hydrocarbyl ammonium ions are formed in situ by addition to the reaction mass of a compound selected from the group consisting of primary, secondary and tertiary amines. 
     
     
       5. The process of claim 4 in which the amine is tri-n-butylamine. 
     
     
       6. The process of claim 4 in which the amine is tri-iso-pentylamine. 
     
     
       7. The process of claim 1 in which the di-C 1-3  alkyl sulfate is dimethyl sulfate.