Dimethylformamide → HCID 86720683, compound

Participants

Reaction Steps

Oxalyl chloride (0.09 g, 0.06 ml, 0.72 mmol) was added drop wise to a solution of 5-(6-methoxy-4′-sulfamoyl-[1,1′-biphenyl]-3-yl)-3,4-dimethylthiophene-2-carboxylic acid (9f, 0.16 g, 0.36 mmol) in dichloromethane (10 ml) and DMF (0.05 g, 0.06 ml, 0.72 mmol) at 0° C. The reaction mixture was 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. The residue so obtained was dissolved in dry dichloromethane (10 ml) and to this was added triethylamine (0.18 g, 0.25 ml, 1.79 mmol) followed by the addition of N,O-dimethylhydroxylamine hydrochloride (0.07 g, 0.72 mmol) under stirring. The reaction mixture was then stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC. Dichloromethane (10 mL) was added to the reaction mixture. The resultant mixture was washed with water (2×10 ml). The separated organic layer was dried over anhydrous sodium sulphate and concentrated at reduced pressure to get a crude product. The crude product so obtained was purified by column chromatography using 30% ethyl acetate in hexane as an eluent to obtain the title compound 9g (0.12 g, 65%).

Provenance & Evidence