N,N-Dimethylethylenediamine → 4-(beta-Dimethylaminoethyl)amino-3-nitrophenyl methyl sulfone
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)(=[O:4])=[O:3].[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][NH2:19]>CS(C)=O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:19][CH2:18][CH2:17][N:16]([CH3:20])[CH3:15])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)(=[O:4])=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-chloro-3-nitrophenyl methyl sulfone (4 g, 17 mmole) and N,N-dimethylethylenediamine (3.3 g, 37 mmole) in DMSO (20 ml) was stored at 75° C. for 1 hour and poured into crushed ice. The yellow solid precipitate was collected by filtration and was dissolved in ethyl acetate. The organic phase was washed with water-brine mixture twice and brine, dried over sodium sulfate, and evaporated under reduced pressure to give the sulfone (22) (3.8 g, 78%) as a yellow solid. A pure sample (m.p. 130°-131° C.) was obtained by recrystallization from ethyl acetate.