4-Chloroaniline → 1-(4-Chlorophenyl)-3-[1-(3-isopropenylphenyl)-1-methyl-ethyl]urea
Reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][CH:15]=1)[C:7]([N:10]=[C:11]=[O:12])([CH3:9])[CH3:8])([CH3:3])=[CH2:2].[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>ClCCl>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:11]([NH:10][C:7]([C:6]2[CH:13]=[CH:14][CH:15]=[C:4]([C:1]([CH3:3])=[CH2:2])[CH:5]=2)([CH3:9])[CH3:8])=[O:12])=[CH:19][CH:18]=1Participants
4
Procedure
To a solution of 3-isopropenyl α, α-dimethylbenzyl isocyanate 2 (473 mg, 2.35 mmol) in dichloromethane (6 mL) at 0° C. was added 4-chloroaniline (300 mg, 2.35 mmol) in dichloromethane (3 mL). The reaction was stirred until complete consumption of starting materials. The precipitated product was collected by filtration and washed with dichloromethane to give 5b (852 mg, 80%). mp 234-236° C. Yield 80%; 1H NMR (DMSO-d6, 400 MHz) δ 1.58 (s, 6H), 2.08 (s, 3H), 5.06 (s, 1H), 5.36 (s, 1H), 6.64 (s, 1H), 7.20 (d, J=6.4 Hz, 2H), 7.23-7.32 (m, 5H), 7.47 (s, 1H), 8.55 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) δ 22.24, 30.30, 55.0, 113.06, 119.50, 122.35, 123.69, 124.86, 124.95, 128.65, 129.09, 140.11, 140.73, 143.60, 148.95, 154.53; ESI-HRMS for C9H22N2OCl (M+H)+ calcd. 329.1421. found 329.1418.