Methanol → N-2-(2-dimethylaminomethyl-5-methyl-4-thiazolylmethylthio)ethyl-N'-methyl-2-nitro-1,1-ethenediamine
Reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:6][C:7]([CH3:15])=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[CH3:3].CO.[CH3:18][N:19]1[CH:21](SC)[CH:20]1[N+:24]([O-:26])=[O:25].C(OCC)(=O)C.CO.[OH-].[NH4+]>COCCOC>[CH3:3][N:2]([CH2:4][C:5]1[S:6][C:7]([CH3:15])=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:21]([NH:19][CH3:18])=[CH:20][N+:24]([O-:26])=[O:25])[N:9]=1)[CH3:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Following the procedure of Example 5, a stirred solution of 1.38 g. of 2-(2-dimethylaminomethyl-5-methyl-4-thiazolylmethylthio)ethylamine in 10 ml. of methanol was treated with N-methyl-1-methylthio-2-nitroethyleneamine. The reaction mixture was kept at room temperature overnight by which time all solids had dissolved. Thin layer chromatography (silica-10:10:1 ethyl acetate-methanol-ammonium hydroxide) indicated substantially a single product. The reaction mixture was concentrated by evaporation of the me±.hanol and the resulting gummy yellow residue was triturated with several portions of cold ether, thus providing an off-white gum. Repeated trituration with cold 1,2-dimethoxyethane yielded N-2-(2-dimethylaminomethyl-5-methyl-4-thiazolylmethylthio)ethyl-N'-methyl-2-nitro-1,1-ethenediamine formed in the above reaction melting at about 104°-106° C.
Workup
- dissolutionall solids had dissolved
- concentrationThe reaction mixture was concentrated by evaporation of the me±
- customhanol and the resulting gummy yellow residue was triturated with several portions of cold ether
- customthus providing an off-white gum
Sources & evidence
- ORD record
- ord-1032b49acd8243f6a47c30bffe972af2
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04760075
Reaction notes
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