Acetonitrile → N-Methyl-N'-[2-[[3-(N,N-dimethylaminomethyl)phenyl]methylthio]ethyl]-2-nitro-1,1-ethenediamine
Reaktionsgleichung
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][NH2:15])[CH:8]=[CH:9][CH:10]=1)[CH3:3].[N+:16]([CH:19]=[C:20](SC)SC)([O-:18])=[O:17].[C:25](#[N:27])C>>[CH3:25][NH:27][C:20]([NH:15][CH2:14][CH2:13][S:12][CH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH:6]=1)=[CH:19][N+:16]([O-:18])=[O:17]Komponenten
4
Versuchsvorschrift
2-[[3-(N,N-Dimethylaminomethyl)phenyl]methylthio]ethanamine (3 g) and 1-nitro-2,2-bis(methylthio)ethylene (2.2 g) were heated under reflux in acetonitrile for 7 hours. The solvent was removed and the residual oil used without further purification. The oil was treated with ethanolic methylamine (33%, 34 ml) and heated under reflux for 3 hours. The solvent was removed and the residual oil was purified by column chromatography on silica with methanol. The resultant orange oil was triturated with ether to give the title compound as a white crystalline solid (0.23 g) m.p. 62°-4°. TLC silica; ethyl acetate:isopropanol:water:0.88 ammonia (25:15:8:2) Rf 0.36.
Aufarbeitung
- customThe solvent was removed
- customthe residual oil used without further purification
- additionThe oil was treated with ethanolic methylamine (33%, 34 ml)
- temperatureheated
- temperatureunder reflux for 3 hours
- customThe solvent was removed
- customthe residual oil was purified by column chromatography on silica with methanol
- customThe resultant orange oil was triturated with ether
Quellen und Nachweise
- ORD-Eintrag
- ord-dd218aad07284402a56b77548753f26c
- Quelldatensatz
- uspto-grants-1991_06
- Patentnummer
- US05021429
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