4,4-Diaminodiphenylmethane → 1-(4-Nitrophenyl)-3-[4-[[4-[(4-nitrophenyl)carbamothioylamino]phenyl]methyl]phenyl]thiourea
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[S:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:13]1[C:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)=[CH:17][CH:16]=[C:15]([NH2:27])[CH:14]=1>O1CCOCC1>[CH2:19]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[S:12])=[CH:22][CH:21]=1)[C:18]1[CH:13]=[CH:14][C:15]([NH:27][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[S:12])=[CH:16][CH:17]=1Participants
4
Procedure
A solution of 4-nitrophenyl isothiocyanate (0.45 g, 2.52 mmol) in dioxane (25 mL) is slowly added, with magnetic stirring, to a solution of 4,4'-diaminodiphenyl methane (0.25 g, 1.26 mmol) in dioxane (10 mL). After 24 hours of stirring at room temperature, the solvent is removed by vacuum evaporation. The solid obtained is washed with n-hexane (3×25 mL) and isopropanol (3×10 mL). Next, the solid is dissolved in ethyl acetate (50 mL) and washed with water (3×25 mL). The organic phase is dried with sodium sulfate. The solvent is removed by vacuum evaporation. The titled compound is obtained as a yellow powder. mp: 115° C.