2,6-Diisopropylphenyl isocyanate → 1-(1-Benzenesulfonylcyclopentylmethyl)-3-(2,6-diisopropyl-phenyl)-urea
Reaction equation
[N:1]([C:4]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:13]([CH3:15])[CH3:14])=[C:2]=[O:3].[C:16]1([S:22]([C:25]2([CH2:30][NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[C:16]1([S:22]([C:25]2([CH2:30][NH:31][C:2]([NH:1][C:4]3[C:5]([CH:13]([CH3:15])[CH3:14])=[CH:6][CH:7]=[CH:8][C:9]=3[CH:10]([CH3:11])[CH3:12])=[O:3])[CH2:29][CH2:28][CH2:27][CH2:26]2)(=[O:23])=[O:24])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In a tube, under nitrogen, 157 mg (0.77 mmol) of 2-isocyanato-1,3-diisopropylbenzene is added to a solution of 168 mg (0.7 mmol) of C-(1-benzenesulfonyl-cyclopentyl)-methylamine in 3.5 ml of dichloromethane. The reaction mixture is stirred at RT for 3 h. The solvent is evaporated with a nitrogen stream. The paste obtained is taken up in heptane (5 mL) for crystallization. The white powder obtained is chromatographed on silica gel (dichloromethane then dichloromethane/methanol, 98/2, v/v). The oil obtained is crystallized from heptane. After filtration and drying, 135 mg of 1-(1-benzenesulfonylcyclopentylmethyl)-3-(2,6-diisopropyl-phenyl)-urea is obtained in the form of a white powder (m.p.=124° C., Yield=44%).