1,1-Bis(methylthio)-2-nitroethylene → HCID 70471124, compound

HRID 370581Notes

Reaction equation

HRID 370581 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[O:13][C:14]([CH2:17][N:18]([CH3:20])[CH3:19])=[CH:15][CH:16]=1)=[O:6].[CH3:24][S:25][C:26](SC)=[CH:27][N+:28]([O-:30])=[O:29]>C(O)C>[CH3:24][S:25][C:26]([NH:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[O:13][C:14]([CH2:17][N:18]([CH3:19])[CH3:20])=[CH:15][CH:16]=1)=[O:6])=[CH:27][N+:28]([O-:30])=[O:29]

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 13269217HCID 13269217, compound

Product 1

HCID 70471124HCID 70471124, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to the above procedure, by reacting 0.02 mol of 3-amino-N-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]benzamide and 0.02 mol of 1,1-bis-methylthio-2-nitroethene in 50 ml of ethanol, the 3-[N-(1-methylthio-2-nitroethenyl)amino]-N-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]benzamide is obtained in 65% yield, said compound being then dissolved in ethanol and treated with a 33% solution of methylamine in ethanol to give the 3-[N-(1-methylamino-2-nitroethenyl)amino]-N-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]benzamide as a practically pure oil. The product thus obtained is transformed into its oxalate in 95% ethanol. After crystallization from 200 ml of ethanol, the pure oxalate is obtained in 43% yield; m.p. 175°-177° C.

Sources & evidence

ORD record
ord-81b5bbfcee274bb6aa56d34b99abaee9
Source dataset
uspto-grants-1985_07
Patent number
US04526995

Reaction notes

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