GB1053997A - - Google Patents

Abstract

1,053,997. Aminobenzaldehydes containing cyclic imide groups. IMPERIAL CHEMICAL INDUSTRIES Ltd. May 18, 1965 [June 23, 1964], No. 25930/64. Heading C2C. [Also in Division C4] Aldehydes of the formula wherein R is a group having 2-4 C atoms between Z and the -CO-, Z is -CO- o, -SO 2 -, A is optionally substituted alkylene, X is cycloalkyl or optionally substituted alky and ring B may be further substituted by halogen, alkyl, alkoxy or acylamino, provided the compounds are free of -SO 3 H and -COOH groups, are obtained by reacting compounds of the formula with phosphorus oxychloride in dimethylformamide. The compounds of Formula II may themselves be obtained by reacting the alkali metal salt of an acid imide with a N-(halogenoalkyl) - N - substituted aniline or by reacting a N-hydroxymethylimide of a dicarboxylic or sulphocarboxylic acid with an N-substituted aniline or by reacting the anhydride of a dicarboxylic acid with an N-(#-aminoethyl)-N-substituted aniline. Examples are given in which the following aldehydes are prepared: (1) 2 - methyl - 4 - [N - ethyl - N - (# - phthalimidoethyl) amino] benzaldehyde, (2) 2-methyl-4- [N - ethyl - N - (# { o - sulphobenzimido } -ethyl) amino] benzaldehyde, 2 - methyl - 4 - [N - ethyl- N - (# - succinimido - ethyl) amino] benzaldehyde, 2 - methyl - 4 - [N - ethyl - N - (# - {4<SP>1</SP>- chlorophthalimido} - amino] benzladehyde, 4 - [N - methyl - N - (# - phthalimidoethyl) amino] - benzaldehyde and 4 - [N : N - di - (#- succinimidoethyl) amino] - benzaldehyde, (3) 4 - [N - ethyl - N - (phthalimido - ethyl) amino] benzaldehyde, (6) 2 - methyl - 4 - [N - (#-methoxyethyl) - N - (# - phthalimidoethyl) amino] benzaldehyde, (7) 2 - methyl - 4 - [N - (# - ethoxycarbonyl - ethyl) - N - (# - phthalimidoethyl) amino] benzaldehyde, (8) 2 - methyl - 4 - N - (# - acetyloxyethyl) - N - (# - phthalimidoethyl) amino] benzaldehyde, (9) 2 - methyl - 4 - [N ethyl - N - (# - 1: 8 - naphthalimidoethyl) amino] benzaldehyde, (10) 2 - methyl - 4 - [N- ethyl - N - (# - hexahydrophthalimidoethyl) amino] benzaldehyde and (11) aldehyde obtained from the specified amines.