Dimethylformamide → HCID 86705022, compound

Participants

Reaction Steps

Oxalyl chloride (2.1 g, 1.4 ml, 16.2 mmol) was added dropwise at 0° C. to a solution of 5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid (compound 1c, 2.2 g, 5.4 mmol) in a mixture of dichloromethane (40 ml) and DMF (0.8 g, 0.8 ml, 10.8 m mol). The resulting mixture was allowed to warm to room temperature and stirred for 1.5 hr, under a nitrogen atmosphere. The progress of reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure and used directly for further reaction. The residue so obtained was dissolved in dry dichloromethane (40 ml) and to this was added triethylamine (2.8 g, 3.9 ml, 27.0 mmol) followed by the addition of N, O-dimethylhydroxylamine hydrochloride (1.06 g, 10.8 mmol) under stirring. The reaction mixture was stirred at room temperature for 2 hr. The progress of reaction was monitored by TLC. The reaction mixture was washed with water (2×20 ml) and the organic layer obtained was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product. The crude product was further purified by column chromatography over silica gel (100-200 mesh) using 80% ethylacetate in hexane as an eluent to obtain the title compound (2.36 g, 86%).

Provenance & Evidence