1,1-Bis(methylthio)-2-nitroethylene → 1-(6-Chloro-3-pyridylmethyl)amino-1-methylthio-2-nitroethylene

HRID 2187225Notes

Reaction equation

HRID 2187225 reaction equation
[CH3:1][S:2][C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].[Cl:10][C:11]1[N:16]=[CH:15][C:14]([CH2:17][NH2:18])=[CH:13][CH:12]=1>CCO>[Cl:10][C:11]1[N:16]=[CH:15][C:14]([CH2:17][NH:18][C:3]([S:2][CH3:1])=[CH:4][N+:5]([O-:7])=[O:6])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 70209275-(Aminomethyl)-2-chloropyridine

Product 1

HCID 855929321-(6-Chloro-3-pyridylmethyl)amino-1-methylthio-2-nitroethyleneYield 47.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 100 ml of EtOH were added 2.4 g (1.5×10−2 mole) of 1,1-bis(methylthio)-2-nitroethylene and 1.4 g (9.8×10−3 mole) of 6-chloro-3-pyridylmethylamine and the mixture was refluxed for 2 hours. The EtOH was distilled off and the residue was subjected to silica gel column chromatography using CH2Cl2 as an eluent. The procedure gave 1.2 g of the title compound as a pale yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. distillationThe EtOH was distilled off

Sources & evidence

ORD record
ord-75795a3a4793454392e59a1079faa758
Source dataset
uspto-grants-2002_06
Patent number
US06407248B1

Reaction notes

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