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

HRID 979788Notes

Reaction equation

HRID 979788 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].[N+:15]([CH:18]=[C:19](SC)[S:20][CH3:21])([O-:17])=[O:16]>ClC=C(Cl)Cl>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:19]([S:20][CH3:21])=[CH:18][N+:15]([O-:17])=[O:16])=[CH:7][CH:6]=1)[CH3:1]

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 79.9%

Reagents, catalysts & solvents 1

HCID 6575TrichloroethyleneSolvent

Procedure

2-[[[5-(Dimethylamino)methyl-2-furanyl]methyl]-thio]ethylamine (21.4 g; 0.1 mol) dissolved in trichloroethylene (200 ml) was added to a solution of 1-nitro-2,2-bis(methylthio)ethene (16.5 g; 0.1 mol), during about 30 minutes, under boiling. Boiling was continued for a further 90 minutes, then solvent was evaporated off under reduced pressure and the residue was chromatographed on silica gel, eluting with petroleum ether/dichloromethane. The product was already pure enough for the subsequent step (26.5 g; 79.9% yield).

Workup

  1. customsolvent was evaporated off under reduced pressure
  2. customthe residue was chromatographed on silica gel
  3. washeluting with petroleum ether/dichloromethane

Sources & evidence

ORD record
ord-d38d25985b2446b3aaf4f28e5d407bc2
Source dataset
uspto-grants-1987_01
Patent number
US04634701

Reaction notes

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