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

HRID 1091072Notes

Reaction equation

HRID 1091072 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-2fb33fef6e5040c7ab9e9f3bbed36727
Source dataset
uspto-grants-1992_01
Patent number
US05084467

Reaction notes

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