Acetonitrile → Ranisen

HRID 127330Notes

Reaction equation

HRID 127330 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-953fea2e5cbd461c9dff63f54f6949c9
Source dataset
uspto-grants-1981_03
Patent number
US04255440

Reaction notes

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