Dimethylformamide → HCID 11724470, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (13.5 g, 0.05 mole), diethoxymethane (7.8 g, 0.075 mole) and dimethylformamide (5.5 g, 0.075 mole) in acetonitrile, under N2, is treated with phosphorous oxychloride (11.5 g, 0.075 mole) over a 0.25 hour period at 39°-45° C., heated at 39°-45° C. for 0.75 hour and treated dropwise with triethylmine (10.1 g, 0.10 mole) at 45°-55° C. over a 0.5 hour period. The reaction mixture is diluted with water, stirred for 16 hours at 25° C. and concentrated in vacuo to give a crude product. The crude material is stirred at reflux temperature with a mixture of toluene and dilute aqueous NaOH and cooled to room temperature. The phases are separated and the organic phase is concentrated in vacuo to give the title product as a solid, mp 83°-84.5° C., 13.1 g, 80 % yield, identified by mass spectral analysis.

Provenance & Evidence