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

HRID 1457898Notes

Reaction equation

HRID 1457898 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-cbba4023cdbe471ca3a7a1ccb1e249f7
Source dataset
uspto-grants-1998_12
Patent number
US05849768

Reaction notes

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