Triethylamine → HCID 178522346, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-aminopyrazole (60 g, 0.722 mol, ABCR) in acetonitrile (500 ml) at 0° C. (ice/brine bath) was added, dropwise, triethylamine (201 ml, 1.44 mol) at such a rate to keep the temperature below 5° C. The reaction mixture was stirred at 0° C. for 0.5 h then a solution of 2,6-difluorobenzoyl chloride (127.5 g, 0.722 mol, Aldrich) in acetonitrile (200 ml) was added over approximately 1 h, keeping the temperature between 0-7° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure and the residue partitioned between water (250 ml) and EtOAc (500 ml). Some solid formed at the interface, this was filtered off and turned out to be product—combined with isolated product at the end for drying. The aqueous layer was separated and extracted with EtOAc (2×500 ml). The combined organics were washed with water (500 ml), dried (MgSO4), charcoaled, filtered and concentrated under reduced pressure to give a yellow solid. The combined residues were triturated with DCM (500 ml) then water (100 ml) and the solid collected by filtration and dried on the sinter, then under high vacuum overnight to give the title compound as a white solid (108.5 g);

Provenance & Evidence