Benzoyl chloride → HCID 20501035, compound

Participants

Reaction Steps

A solution of benzoyl chloride (0.63 g.) in 1,2-dimethoxyethane (10 ml.) was added dropwise to a stirred mixture of 1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (1.8 g.) and triethylamine (0.51 g.) in 1,2-dimethoxyethane (50 ml.) cooled at 0°-5° C. When the addition was completed, the solution was stirred at 20°-25° C. for three hours. Silica gel (5 g., Merck type 7734) was added to the solution and the mixture was evaporated The residue obtained was added to the top of a column of silica gel (75 g., Merck type 7734) made up in toluene. The column was eluted with increasing concentration of ethyl acetate in toluene up to 25% v/v and the fractions containing the major product [Relative flow value: 0.4, on Merck SiO2TLC plates No. 5715; eluant: EtOAc/Toluene, 1:1 v/v] were collected, combined and evaporated. The solid thereby obtained was recrystallised from ethyl acetate/petrol 60-80 to give 3-benzoyl-1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (0.34 g.), m.p. 251°-253° C.

Provenance & Evidence