Dimethylformamide → HCID 19011120, compound

Participants

Reaction Steps

A solution of thionyl chloride (2.42 ml, 33 mmole) in dichloromethane (10 ml) was added dropwise over 5 minutes to a suspension of the product of step b) (10.59 g, 30 mmole) in dichloromethane (90 ml) containing N,N-dimethylformamide (0.2 ml), stirred at reflux under an atmosphere of nitrogen. After 2 hours, solvent was removed from the resulting yellow solution by distillation, approximately 85 ml distillate being collected. Dilution of the residue with methyl t-butyl ether was followed by stirring at 15° C. for 30 minutes prior to collection of the solid precipitate by filtration. After washing with methyl t-butyl ether (2×20 ml), 4-(5-methoxycarbonyl-1-methylindol-3-ylmethyl)-3-methoxybenzoyl chloride was obtained as an off-white solid, 10.10 g (90.6%); m.p. 147°-149° C.; NMR (250 MHz, DMSO-d6): 3.76, 3.92, 3.97 (each s, 3H, NCH3 plus OCH3 plus CO2CH3), 4.16 (s, 2H, ArCH2Ar'), 6.87 (s, 1H), 7.20 (d, 1H), 7.29 (d, 1H), 7.54 (d, 1H), 7.66 (dd, 1H), 7.92 (dd, 1H), 8.32 (d, 1H).

Provenance & Evidence