Oxalyl chloride → HCID 11161080, compound

Participants

Reaction Steps

Oxalyl chloride (12.7 g; 0.1 mol) was added dropwise to the stirring solution of N-ethyl-N′-(4-fluorophenyl) thiourea (16 g; 0.08 mol) in methylene chloride (200 mL). The mixture was heated at reflux for 1 hour then evaporated to dryness. Ethanol (200 mL) was added and the mixture was heated at reflux for 1 hour then evaporated to dryness. The residue was dissolved in ethyl acetate (500 mL) and washed with 2N hydrochloric acid (2×400 mL) then with water (400 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was crystallized from ethyl acetate/hexane to give 19.1 g of 1-ethyl-3-(4-fluorophenyl)-2-thioxo-4,5-imidazolidinedione, m.p. 172–174° C. Mass spectrum; FAB (M+H)+ m/z 253. 1H-NMR (DMSO-d6; 300 MHz): δ 7.42–7.34 (m, 4H), 3.92 (q, 2H), and 1.22 ppm (t, 3H).

Provenance & Evidence