Acetonitrile → Ranisen

HRID 426498Notes

Reaction equation

HRID 426498 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:3].CS[C:17](SC)=[CH:18][N+:19]([O-:21])=[O:20].[C:24](#[N:26])C>>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:17]([NH:26][CH3:24])=[CH:18][N+:19]([O-:21])=[O:20])=[CH:7][CH:6]=1)[CH3:1]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine

Product 1

HCID 5039Ranisen

Procedure

2-[[[5-(Dimethylamino)methyl-2-furanyl]methyl]thio]ethanamine (4.25 g) and 1,1-bis(methylthio)-2-nitroethene (3.3 g) were refluxed in acetonitrile (50 ml) for 14 hr. Solvent was removed and the residue dissolved in 36% methanolic methylamine (50 ml) and the solution refluxed for 8 hr. Solvents were removed and the residue in methanol treated with charcoal. Filtration and evaporation of the solvent gave the title compound as Example 15 (5.0 g).

Workup

  1. customSolvent was removed
  2. dissolutionthe residue dissolved in 36% methanolic methylamine (50 ml)
  3. temperaturethe solution refluxed for 8 hr
  4. customSolvents were removed
  5. additionthe residue in methanol treated with charcoal
  6. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-a26b403ccdef47c7a2a5081e28842ca3
Source dataset
uspto-grants-1979_10
Patent number
US04169855

Reaction notes

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