4-Methylphenyl isocyanate → N-(2-methylcarbamoyl-5-tert-butyl-3-pyrrolyl)-N'-(4-methylphenyl)urea
Reaction equation
[CH3:1][NH:2][C:3]([C:5]1[NH:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH2:10])=[O:4].[C:15]1([CH3:24])[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1>C(Cl)Cl>[CH3:1][NH:2][C:3]([C:5]1[NH:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH:10][C:22]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([CH3:24])=[CH:16][CH:17]=1)=[O:23])=[O:4]Participants
4
Procedure
To a solution of 2-(N-methylcarbamoyl)-3-amino-5-tert-butylpyrrole (0.14 g, 0.70 mmol) in CH2Cl2 (5 mL) at room temp. was annd p-tolyl isocyanate (0.088 mL, 0.70 mmol, 1.0 equiv) and the resulting mixture was allowed to stir at room temp. overnight. The resulting precipitate was separated and washed with CH2Cl2 to give N-(2-methylcarbamoyl-5-tert-butyl-3-pyrrolyl)-N′-(4-methylphenyl)urea (0.17 g, 74%): mp 164-166° C.; 1H-NMR (DMSO-d6) δ1.23 (s, 9H), 2.19 (s, 3H), 2.75 (d, J=4.41 Hz, 3H), 6.49 (d, J=2.57 Hz, 1H), 7.01 (d, J=8.46 Hz, 2H), 7.33 (d, J=8.46 Hz, 2H), 7.60-7.63 (m, 1H), 9.45 (s, 1H), 9.50 (s, 1H), 10.17 (br s, 1H); FAB-LRMS m/z 329 (M+H).