1,1-Bis(methylthio)-2-nitroethylene → 1-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-1-methylthio-2-nitroethylene

HRID 892796Notes

Reaction equation

HRID 892796 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][NH2:14])[N:9]=1)[CH3:3].[CH3:15][S:16][C:17](SC)=[CH:18][N+:19]([O-:21])=[O:20]>C(#N)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:17]([S:16][CH3:15])=[CH:18][N+:19]([O-:21])=[O:20])[N:9]=1)[CH3:1]

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

Product 1

HCID 678972721-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-1-methylthio-2-nitroethyleneYield 53.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

With 2 ml of acetonitrile were mixed 1 g of 2-{[2-(dimethylamino)methyl-4-thiazolyl]methylthio}ethylamine and 1.4 g of 1,1-bis(methylthio)-2-nitroethene, and the resulting mixture was subjected to reaction under reflux for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and 5 ml of ethanol was added to the resulting residue, after which the insolubles were removed by filtration. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography (Wako Silica Gel C-200, eluent; chloroform:ethanol=20:1 by volume) to obtain 0.8 g (yield 53%) of oily 1-{2-[[2-(dimethylamino)methyl-4-thiazolyl]methylthio]ethylamino}-1-methylthio-2-nitroethene.

Workup

  1. customthe resulting mixture was subjected to reaction
  2. temperatureunder reflux for 2 hours
  3. customAfter completion of the reaction
  4. customthe solvent was removed by distillation under reduced pressure, and 5 ml of ethanol
  5. additionwas added to the resulting residue
  6. customafter which the insolubles were removed by filtration
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe residue thus obtained
  9. customwas purified by a column chromatography (Wako Silica Gel C-200, eluent; chloroform:ethanol=20:1 by volume)

Sources & evidence

ORD record
ord-d0333fbf084b42ff8da857240af649b4
Source dataset
uspto-grants-1992_06
Patent number
US05120746

Reaction notes

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