Acetonitrile → Ranisen

HRID 65765

Reaction equation

HRID 65765 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-590ae28d589b41ae960292662b4c4b89
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Linked notes

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