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

US3931311A · kind A · utility

Assignee

• BAYER HEALTHCARE LLC · DE

Inventors

• Rudolf Thomas · Haan, DE
• Wolfgang Kramer · Wuppertal, DE
• Ludwig Eue
• Carl Metzger · Köngen, DE
• Gerhard Jager · Leverkusen, DE

Key dates

• Filing date: Feb 21, 1973
• Grant date: Jan 6, 1976
• Expiry date: Feb 21, 1993

Classification

• Technology area (CPC D): Textiles; Paper
• CPC primary: D06P1/6491
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Novel N,N',N'-trisubstituted N-halogenomethylurea compounds of the formula: ##EQU1## in which R.sup.1 is alkyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, aryl or aralkyl (each of which may be optionally substituted), PA1 R.sup.2 is alkyl, alkenyl, alkynyl or alkoxy (each of which may be optionally substituted), or halogenoalkyl or cycloalkyl, PA1 R.sup.3 is alkyl (which may be optionally halogen-substituted), alkenyl or alkynyl, or PA1 R.sup.2 and R.sup.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, PA1 X is oxygen or sulfur, and PA1 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.sup.1, R.sup.2, R.sup.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.degree. to +150.degree.C, optionally in the presence of a diluent and, as a catalyst, a proton-relea…