1,1-Bis(methylthio)-2-nitroethylene → 1-{1-(2-Chloro-5-pyridyl)ethylamino}-1-methylthio-2-nitroethylene

HRID 1291931Notes

Reaction equation

HRID 1291931 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[CH:4][N:3]=1.[CH3:11][S:12][C:13](SC)=[CH:14][N+:15]([O-:17])=[O:16]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:13]([S:12][CH3:11])=[CH:14][N+:15]([O-:17])=[O:16])[CH3:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 157456051-(6-Chloropyridin-3-yl)ethan-1-amine

Product 1

HCID 727435041-{1-(2-Chloro-5-pyridyl)ethylamino}-1-methylthio-2-nitroethyleneYield 40.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(2-chloro-5-pyridyl)ethylamine (4.7 g), 1,1-bis-methylthio-2-nitroethylene (5.0 g) and ethanol (50 ml) was refluxed under heating until the generation of mercaptan ceased. Then, the ethanol was distilled off from the mixture under reduced pressure and the resulting residue was purified on a chromatographic column (the eluent mixture=ethanol+chloroform) to obtain the desired 1-{1-(2-chloro-5-pyridyl)ethylamino}-1-methylthio-2-nitroethylene (3.3 g) having a melting point in the range of from 136° to 140° C.

Workup

  1. temperaturewas refluxed
  2. distillationThen, the ethanol was distilled off from the mixture under reduced pressure
  3. customthe resulting residue was purified on a chromatographic column (the eluent mixture=ethanol+chloroform)

Sources & evidence

ORD record
ord-b639520c654a45cab219842449056a37
Source dataset
uspto-grants-1998_05
Patent number
USRE035811

Reaction notes

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