Dimethylformamide → HCID 178440443, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-isopropyl-4-nitro-2H-pyrazole-3-carboxylic acid (Farmaco, 46, 11, 1991, 1337-1350) (6 g, 0.03 mol) in N,N-dimethylformamide (69 μL) and dichloromethane (67 mL) was cooled to −5° C. in ice/acetone. Oxalyl chloride (11.48 g, 0.09 mol) was added over 30 minutes and the reaction mixture stirred for 1 hour, the reaction mixture was then allowed to return to room temperature for 2 hours. The reaction mixture was concentrated in vacuo and remaining solvent azeotroped with dichloromethane. The resulting solid was suspended in tetrahydrofuran (70 mL), cooled to 0° C. and 0.880 ammonia (25 mL) added. The reaction mixture was stirred for 30 minutes and then concentrated in vacuo. The resulting solid was suspended in water, filtered and dried at 70° C. under vacuum to yield the product.

Provenance & Evidence