Dimethylamine → HCID 178484500, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-nitro-1H-pyrazole-3-carboxylic acid (1.0 g, 6.4 mmol) in dichloromethane (20 ml) was treated with thionyl chloride (1.4 ml, 19 mmol) and a drop of DMF at ambient temperature. The reaction mixture is stirred at 40° C. overnight whereupon another equivalent of thionyl chloride (0.46 ml, 6.4 mmol) was added and stirring was continued at 40° C. for another 24 h. All volatiles were removed and the acid chloride was suspended in dichloromethane (6 ml) and cooled to 0° C. Triethylamine (4.44 ml, 31.8 mmol) and dimethylamin (4.14 ml, 2M solution in THF) were added. The reaction mixture was allowed to warm-up to ambient temperature and stirring was continued for 3 h. The reaction mixture was partitioned between potassium hydrogen sulfate (20 ml, 10% aqueous solution) and ethyl acetate (40 ml) and extracted. The organic phase was washed with water and brine, dried and the solvent was evaporated. The crude product was triturated with diethylether, sucked off and dried to yield a light brown solid (0.35 g, 30%).

Provenance & Evidence