Methanol → 1-(2-chloro-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea

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Reaction Conditions

Reaction Steps

Commercially available 2-chloro-4-trifluoromethylbenzylamine (700 mg, 3.3 mmol) was dissolved in 20 ml of AcOEt and at 0° C. triphosgene (989 mg, 3.3 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1a (319 mg, 2.14 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt 9.5/MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 140 mg of a white solid. Yield=18% 1HNMR (DMSO, 400 MHz) δ 4.44 (2H, d, J=5.6 Hz), 6.64 (1H, d, J=7.2 Hz), 6.84 (1H, t, J=8.4 Hz), 6.89 (1H, t), 6.96 (1H, d, J=8 Hz), 7.64 (1H, d, J=8.4 Hz), 7.74 (1H, d), 7.86 (1H, s), 8.43 (1H, bs), 9.99 (1H, bs), 10.61 (1H, bs); [M+1] 385.0 (C16H12ClF3N4O2 requires 384.74).

Provenance & Evidence