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

HRID 728988Notes

Reaction equation

HRID 728988 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, theethanol 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, theethanol 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-82b03bc4d3b149869312c559bdf2b66a
Source dataset
uspto-grants-1991_09
Patent number
US05051434

Reaction notes

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