Ethoxalyl chloride → 1-(2,4-Difluoro-phenyl)-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidine-4,5-dione

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Reaction Steps

Ethyl chlorooxoacetate (0.53 mL, 4.77 mmol) was added to a stirring solution of the above thiourea (1.00 g, 3.67 mmol) in dichloromethane (15 mL) and the resulting mixture was stirred overnight at room temperature. Concentration, trituration of the residue with diethyl ether, and recrystallization from boiling methanol afforded 0.75 g (62%) of 1-(2,4-difluoro-phenyl)-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidine-4,5-dione as a yellow solid: mp 155.2–156.0° C.; 1H NMR (DMSO-d6): δ 7.55 (m, 2H), 7.30 (m, 1H), 4.80 (m, 1H), 1.51 (d, 3H), 0.99 (s, 9H); IR (KBr): 3550, 2970, 2230, 1770 cm1; MS (m/z) 326 (M+).

Provenance & Evidence