4-(4-methyl-1H-imidazol-5-yl)butan-1-amine → 1-Methylthio-1-[4-(5-methylimidazol-4-yl)butylamino]-2-nitroethylene
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][C:10]=1[CH3:11].[CH3:12][S:13]([C:15](SC)=[CH:16][N+:17]([O-:19])=[O:18])=O>>[CH3:12][S:13][C:15]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][C:10]=1[CH3:11])=[CH:16][N+:17]([O-:19])=[O:18]Participants
3
Procedure
Reaction of 4-(4-aminobutyl)-5-methylimidazole (see Example 7 (ii), 0.765 g, 0.005 mol) with 1-methylsulphinyl-1-methylthio-2-nitroethylene(0.91 g, 0.005 mol), gave 1-methylthio-1-[4-(5-methylimidazol-4-yl)butylamino]-2-nitroethylene (0.69 g, 51%) which was treated directly with methylamine to yield 1-methylamino-b 1-[4-(5-methylimidazol-4-yl)butylamino]-2-nitroethylene (0.40 g, 61.9%). This compound was reacted with picric acid to give 1-methylamino-1-[4-(5-methylimidazol-4-yl)butylamino]-2-nitroethylene picrate hemihydrate (0.33 g, 26.3% last stage), m.p. 185°-187°.
Sources & evidence
- ORD record
- ord-411e41f02f0b4b12b5b3fab591e2cee7
- Source dataset
- uspto-grants-1979_08
- Patent number
- US04166184
Reaction notes
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