2-{[(Pyridin-3-yl)methyl]sulfanyl}ethan-1-amine → N-[3-[5-[(Dimethylamino)methyl]-2-furanylmethoxy]propyl]-2-nitro-N'-[2-[(3-pyridinylmethyl)thio]ethyl]-1,1-ethenediamine
Reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][C:4]1[O:5][C:6]([CH2:9][O:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](SC)=[CH:16][N+:17]([O-:19])=[O:18])=[CH:7][CH:8]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][S:30][CH2:31][CH2:32][NH2:33])[CH:24]=1>>[CH3:22][N:2]([CH2:3][C:4]1[O:5][C:6]([CH2:9][O:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([NH:33][CH2:32][CH2:31][S:30][CH2:29][C:25]2[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=2)=[CH:16][N+:17]([O-:19])=[O:18])=[CH:7][CH:8]=1)[CH3:1]Participants
3
Procedure
A mixture of N,N-dimethyl-5-[[3-[(1-methylthio-2-nitroethenyl)amino]propoxy]methyl]-2-furanmethanamine (0.7 g) and 2-[(3-pyridinylmethyl)thio]ethanamine (0.36 g) was heated at 98°-100° for 3 hr. The oily residue was chromatographed (silica/methanol-0.88 ammonia 79:1) and the appropriate eluate evaporated to dryness to give the title compound as a hemihydrate as an oil (0.52 g).
Workup
- temperaturewas heated at 98°-100° for 3 hr