Dimethylcarbamoyl Chloride → HCID 22387277, compound

Participants

Reaction Steps

Dimethylcarbamyl chloride (83 mg) was added to a stirred solution of methyl N-(3,4-dichlorobenzyl)-4-hydroxyindole-2-carboxylate (150 mg), triethylamine (65 mg) and DMAP (5 mg) in dichloromethane. The reaction was stirred for 16 hours at room temperature under an atmosphere of nitrogen. The reaction was washed with hydrochloric acie (2M, 70 ml), saturated aqueous sodium hydrogencarbonate solution, water and saturated sodium chloride solution. Combined organic extracts were dried (MgSO4), concentrated in vacuo and the residue purified by column chromatography using 60% ethyl acetate:iso-hexane as eluent to give the product as a colourless gum (132 mg,74%); NMR d (CD3SOCD3) 2.94 (s, 3H), 3.12 (s, 3H), 3.81 (s, 3H), 5.82 (s, 2H), 6.91 (m, 2H), 7.21 (s, 1H), 7.27-7.36 (m, 2H), 7.46 (d, 1H), 7.52 (d, 1H); M/z (+) 421 (MH+).

Provenance & Evidence