Triethylamine → HCID 22609789, compound

Participants

Reaction Conditions

Reaction Steps

Sulphuryl chloride (3.4 ml, 5.71 g, 42.4 mmol) was added via syringe to a stirred solution of ethyl 2-(methylthio)acetate (5.4 ml, 5.63 g, 42.0 mmol) in dry dichloromethane (30 ml) cooled to −78° C., under a nitrogen atmosphere. After stirring for 15 min, a solution of 4-cyanoaniline (5.0 g, 42.3 mmol) and 1,8-bis(dimethylamino) naphthalene (9.0 g, 42.0 mmol) in dry dichloromethane (50 ml) was added maintaining the temperature at −78° C. Stirring was continued for 3 hours at −78° C., and then triethylamine (5.9 ml, 4.28 g, 42.3 mmol) was added at −78° C., and then the mixture was allowed to warm to room temperature. Stirring was continued under a nitrogen atmosphere for 3 days. Glacial acetic acid (5.0 ml, 5.25 g, 87.3 ml) was then added and the mixture was stirred for 1 hour. The reaction mixture was washed with 8% aq. NaHCO3 (50 ml) and water (2×100 ml), dried (Na2CO3), and concentrated in vacuo. Silica gel chromatography, eluting with 1:2 ethyl acetate/i-hexane, gave 5-cyano-3-methylthio-2-oxoindole as a yellow solid (2.8 g, 13.7 mmol, 32%); δH CDCl3 8.95 (1H,br s), 7.67 (1H,s). 7.60 (1H,d), 7.01 (1H,d), 4.30 (1H,s), 2.08 (3H,s).

Provenance & Evidence