3-Bromoaniline → HCID 59540876, compound

Participants

Reaction Steps

A solution of 3-bromo-phenylamine (1.0 g, 5.81 mmol) and 3-carboxymethyl-tetrahydro-thiophene-3-carboxylic acid (1.15 g, 6.05 mmol, [Rice, L. M. et al; J. Med Chem; 6; 1963; 388-402]) in xylene (10 ml) was heated for 2 hours (oil bath, 180° C.) with fitted Dean-Stark trap to remove water. The material was cooled to ambient and the xylene stripped (rotovap/pump). The material was covered with dry CH2Cl2 (10 ml). Carbonyldiimidazole (1.18 g, 7.26 mmol) was added with vigorous stirring and a homogeneous solution was rapidly obtained. After over night stirring the material was adsorbed onto silica (12 g). The crude was purified by chromatography on silica gel, eluting with a gradient of 100% CH2Cl2 to 0.12% MeOH/CH2Cl2, to afford 1.76 g of 7-(3-bromo-phenyl)-2-thia-7-aza-spiro[4.4]nonane-6,8-dione as a light yellow solid.

Provenance & Evidence