1,1-Bis(methylthio)-2-nitroethylene → N-((6-chloropyridin-3-yl)methyl)-N-ethyl-1-(methylthio)-2-nitroethenamine

HRID 1043518Notes

Reaction equation

HRID 1043518 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[N+:12]([CH:15]=[C:16](SC)[S:17][CH3:18])([O-:14])=[O:13]>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:10][CH3:11])[C:16]([S:17][CH3:18])=[CH:15][N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 11137568N-((6-Chloropyridin-3-yl)methyl)ethanamine

Product 1

HCID 54422628N-((6-chloropyridin-3-yl)methyl)-N-ethyl-1-(methylthio)-2-nitroethenamineYield 20.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 100 ml three necked round bottom flask was added N-((6-chloropyridin-3-yl)methyl)ethanamine (17.0 g, 0.1 mol), (2-nitroethene-1,1-diyl)bis(methylsulfane) (15.0 g, 0.09 mol), dry ethanol (50 mL). The mixture was refluxed. After completion, the reaction mixture was cooled to r.t. and concentrated under reduced pressure to obtain crude product as oil, which was purified by column chromatography to afford 5.3 g N-((6-chloropyridin-3-yl)methyl)-N-ethyl-1-(methylthio)-2-nitroethenamine in 18.5% yield.

Workup

  1. temperatureThe mixture was refluxed
  2. concentrationconcentrated under reduced pressure
  3. customto obtain crude product as oil, which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9199bef9f13a44e7aa1e2e26d175dd72
Source dataset
uspto-grants-2013_10
Patent number
US08563546B2

Reaction notes

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