Dimethylamine → 1-Dimethylamino-1-methylthio-2-nitroethylene

HRID 249512Notes

Reaction equation

HRID 249512 reaction equation
[CH3:1][S:2][C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].[CH3:10][NH:11][CH3:12]>CCO>[CH3:10][N:11]([CH3:12])[C:3]([S:2][CH3:1])=[CH:4][N+:5]([O-:7])=[O:6]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 836231,1-Bis(methylthio)-2-nitroethylene

Product 1

HCID 538966631-Dimethylamino-1-methylthio-2-nitroethylene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 50 ml of EtOH was dissolved 3.3 g of 1,1-bis-(methylthio)-2-nitroethylene and 2.2 ml of a 40% aqueous solution of dimethylamine was added dropwise in 2 portions at 30-minute intervals under refluxing. After completion of dropwise addition, the mixture was further refluxed for 30 minutes. Then, the EtOH was distilled off and the residue was subjected to silica gel column chromatography using CHCl3 --MeOH (20:1) as an eluent. The procedure gave 1.0 g of 1-dimethylamino-1-methylthio-2-nitroethylene as a yellow oil.

Workup

  1. additionwas added dropwise in 2 portions at 30-minute intervals
  2. temperatureunder refluxing
  3. additionAfter completion of dropwise addition
  4. temperaturethe mixture was further refluxed for 30 minutes
  5. distillationThen, the EtOH was distilled off

Sources & evidence

ORD record
ord-937c343f56aa43248bd83aa23db323ab
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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