Ammonia → HCID 59637298, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (50 g, 0.16 mol) in DCM (750 mL), a catalytic amount of DMF was added and the mixture was cooled to 0° C. Thionyl chloride (61 mL, 0.83 mol) was added drop wise for 30 min at 0° C. The overall reaction mixture was heated to reflux and maintained for 2 h. Progress of the reaction was monitored by TLC (10% ethyl acetate/hexane, Rf˜0.4). On disappearance of the starting material, DCM was distilled off completely. Above prepared acid chloride was dissolved in DCM (500 mL) and added drop wise to aqueous ammonia solution (700 mL) at 0° C. The overall reaction mixture was allowed to stir for 1 h and the progress of the reaction was monitored by TLC (10% ethyl acetate/hexane, Rf˜0.7). On completion of the reaction, ice cold water (200 mL) was added and the product was extracted with ethyl acetate (2×200 mL). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to yield 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide as an off white solid (37 g, crude). Crude product obtained was directly used for the next step.

Provenance & Evidence