N,N,N-trisubstituted N-halogenomethylurea and thiourea compounds and process for their preparation

Abstract

Abstract Novel N,N',N'-trisubstituted N-halogenomethylurea compounds of the formula: ##EQU1## in which R 1 is alkyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, aryl or aralkyl (each of which may be optionally substituted), R 2 is alkyl, alkenyl, alkynyl or alkoxy (each of which may be optionally substituted), or halogenoalkyl or cycloalkyl, R 3 is alkyl (which may be optionally halogen-substituted), alkenyl or alkynyl, or R 2 and R 3 jointly represent an alkylene bridge which, can be interrupted by one or more hetero-atoms, such as S or O, or by the NH group, and which forms a heterocyclic ring with the adjoining nitrogen atom, X is oxygen or sulfur, and Y is chlorine or bromine. Are prepared by reacting a N,N',N'-trisubstituted urea or thiourea of the general formula: ##EQU2## in which R 1 , R 2 , R 3 and X have the above-mentioned meanings, is reacted, per mole thereof, with at least 1 mole of formaldehyde (which may be formed in situ from a formaldehyde-releasing substance) and a halogenating agent at a temperature of from -10° to +150°C, optionally in the presence of a diluent and, as a catalyst, a proton-releasing compound (for example a hydrogen halide) or a Lewis acid.

Inventors

• 👤 Rudolf Thomas
• 👤 Wolfgang Kramer
• 👤 Ludwig Eue
• 👤 Carl Metzger
• 👤 Gerhard Jager

Bibliographic Details