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

HRID 236266Notes

Reaction equation

HRID 236266 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-52c8579f4eee4b8ea5835ef33b6e1536
Source dataset
uspto-grants-1987_02
Patent number
US04643849

Reaction notes

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