1,1-Bis(methylthio)-2-nitroethylene → N-{2-[({5-[(Dimethylamino)methyl]furan-2-yl}methyl)sulfanyl]ethyl}-1-(methylsulfanyl)-2-nitroethen-1-amine

HRID 1395375Notes

Reaction equation

HRID 1395375 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].[CH3:15][S:16][C:17](SC)=[CH:18][N+:19]([O-:21])=[O:20]>C(#N)C>[N+:19]([CH:18]=[C:17]([S:16][CH3:15])[NH:14][CH2:13][CH2:12][S:11][CH2:10][C:8]1[O:9][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[CH:6][CH:7]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

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

Product 1

HCID 53427435N-{2-[({5-[(Dimethylamino)methyl]furan-2-yl}methyl)sulfanyl]ethyl}-1-(methylsulfanyl)-2-nitroethen-1-amineYield 63.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[(5-dimethylaminomethyl-2-furyl)methylthio]ethylamine (12.86 g, 60 mmole) [prepared by the procedure described in Belgian Pat. No. 857,388] and 1,1-bis(methylthio)-2-nitroethylene (9.91 g, 60 mmole) [prepared according to the procedure described in Chem. Ber., 100, 591 (1967) and Acta Chem. Scand., 21. 2797 (1967)] in acetonitrile (150 ml) was stirred and heated to reflux temperature under a positive pressure of nitrogen for 15.5 hours. The solvent was removed by evaporation under reduced pressure and the crude product placed on silica gel and chromatographed using a gradient elution of methylene chloride-methanol. The appropriate fractions were combined to yield the title compound (12.6 g).

Workup

  1. customprepared by the procedure
  2. temperatureheated
  3. temperatureto reflux temperature under a positive pressure of nitrogen for 15.5 hours
  4. customThe solvent was removed by evaporation under reduced pressure
  5. customchromatographed
  6. washa gradient elution of methylene chloride-methanol

Sources & evidence

ORD record
ord-7582c528bcbf4e4893e8163180d58655
Source dataset
uspto-grants-1980_05
Patent number
US04203909

Reaction notes

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