Ethanol → HCID 67530883, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-chlorophenyl)isothiocyanate (23.1 g, 136 mmol) and acetonitrile (30 ml) was dissolved in dry THF (200 ml) and cooled to −78° C. under a nitrogen atmosphere. A solution of sodium bis(trimethylsilyl)amide in THF (1.0M, 300 ml, 300 mmol) was added over 10 min and the reaction mixture then stirred with warming to r.t. over 2 h. Ethanol (250 ml) and N,N-dimethyluracil (19.4 g, 136 mmol) were added and the mixture heated to reflux for 24 h. The mixture was cooled and concentrated in vacuo to leave a thick brown oil. The residue was dissolved in acetonitrile (200 ml) and bromonitromethane (23.0 g, 164 mmol) added. The mixture was heated to 55° C. for 18 h then cooled to r.t. and diluted with ice/water (800 ml). The resultant solid was isolated by filtration to give a hard black solid. This was then purified by treatment with hot acetone/water (3:1, 300 ml). Cooling and filtration gave the title compound as a pale orange solid (18.0 g, 41%). δH (DMSO-d6) 8.78-8.52 (2H, br s), 8.31 (1H, d, J 9.7 Hz), 7.83-7.50 (4H, m), 6.64 (1H, d, J 9.7 Hz). LCMS (ES+) RT 3.02 minutes, 322 (M+H)+

Provenance & Evidence