Water → HCID 70574177, compound

Participants

Reaction Steps

A 300 ml reaction flask fitted with a magnetic stirrer, heating mantle, thermometer and water-cooled condenser was charged with 5.0 g (0.016 mole) of 4-bromo-4'-chloro-2-methylacetoacetanilide [M.P. 103°-105°; prepared as described by Hodgkinson and Staskun in The Journal of Organic Chemistry, vol. 34, p. 1710 (1969)], 100 ml of ethanol, 2.5 g (0.017 mole) of N-isobutyrylthiourea [M.P. 112°-114°; prepared as described by Moore and Crossley in The Journal of the American Chemical Society, vol. 62, p. 3273 (1940)] and 1.6 g (0.02 mole) of pyridine. The solution was stirred and refluxed for three hours. The solvent was removed under reduced pressure and the residual solid was stirred with water-toluene. There was obtained 3.9 g (69%) of white solid, M.P. 202°-204°. N.M.R. (dimethyl-d6 sulfoxide)∂ 1.1-1.3 (2×CH3), 1.4- 1.6 (CH3, doublet), 3.5-4.0 (2×CH), 6.8 (hetero-aromatic), 7.2-7.7 (aromatic).

Provenance & Evidence