Cyclopropylamine → N-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl-N'-cyclopropyl 2-nitro-1,1-ethenediamine
Reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15](SC)=[CH:16][N+:17]([O-:19])=[O:18])[N:9]=1)[CH3:3].[CH:22]1([NH2:25])[CH2:24][CH2:23]1>C(O)C>[CH3:3][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15]([NH:25][CH:22]2[CH2:24][CH2:23]2)=[CH:16][N+:17]([O-:19])=[O:18])[N:9]=1)[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A reaction mixture, prepared from 1-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-1-methylthio-2-nitroethylene, cyclopropylamine and ethanol, was heated to refluxing temperature for about three hours. The solvent was then removed by evaporation and the resulting residue was chromatographed over silica using a gradient elution technique. The desired compound was eluted with a 5:95 methanol:ethyl acetate solvent mixture. Removal of the solvent yielded N-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl-N'-cyclopropyl 2-nitro-1,1-ethenediamine which melted at 128.5°-131.5° C. after recrystallization from a methanol/ethyl acetate solvent mixture.
Workup
- temperaturewas heated
- temperatureto refluxing temperature for about three hours
- customThe solvent was then removed by evaporation
- customthe resulting residue was chromatographed over silica using
- washa gradient elution technique
- washThe desired compound was eluted with a 5:95 methanol
- customRemoval of the solvent
Sources & evidence
- ORD record
- ord-2cca6b5a100f4a8892a8feaed54955d1
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04904792
Reaction notes
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