Dimethylformamide → HCID 86720680, compound

Participants

Reaction Steps

Oxalyl chloride (0.87 g, 0.58 ml, 6.94 mmol) was added drop wise to a solution of 5-(6-methoxy-4′-sulfamoyl-[1,1′-biphenyl]-3-yl)-4-methylthiophene-2-carboxylic acid (1c, 1.4 g, 3.47 mmol) in dichloromethane (28 ml) and DMF (0.53 ml, 6.94 mmol) at 0° C. The reaction mixture was then allowed to come to room temperature and stirred for 1.5 hr under nitrogen atmosphere. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure and used directly for further reaction. Residue obtained after concentration was dissolved in dry dichloromethane (20 ml) and to this was added triethylamine (2.1 g, 2.89 ml, 20.8 mmol) followed by the addition of N,O-dimethylhydroxylamine hydrochloride (1.34 g, 13.88 mmol) under stirring. The reaction mixture was stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC. The reaction mixture was then diluted with dichloromethane (100 ml). The mixture obtained was washed with water (2×20 ml), followed by washing with brine (1×20 ml). The separated organic layer 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 using 80% ethyl acetate in hexane as an eluent to obtain the title compound (1.1 g, 63.2%).

Provenance & Evidence