Ethoxalyl chloride → 1-(4-Dimethylamino-phenyl)-3-(2,2-dimethyl-propyl)-2-thioxo-imidazolidine-4,5-dione Hydrochloride

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Reaction Steps

Ethyl chlorooxoacetate (3.4 mL, 30 mmol) was added dropwise to a stirring solution of N-[4-(dimethylamino)phenyl]-N′-(2,2-dimethylpropyl)-thiourea (3.98 g, 15 mmol) in dichloromethane (100 mL) and the resulting mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was treated with ether (100 mL) and the mixture was stirred for one hour. The solid was collected by filtration, washed with fresh ether and dried to give 5.3 g (100%) of the title compound: mp. 244–246° C.; 1H NMR (DMSO-d6): δ7.28 (d, 2H), 7.20 (br s, 2H), 3.74 (s, 2H), 3.02 (s, 6H), and 0.98 ppm (s, 9H); IR (KBr) 3640, 3080, 2350, 1775 cm−1; MS (m/z) 319 (M+).

Provenance & Evidence