Methylamine → 1,1-Ethenediamine, N-[(6-chloro-3-pyridinyl)methyl]-N'-methyl-2-nitro-

HRID 1091064Notes

Reaction equation

HRID 1091064 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](SC)=[CH:11][N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.[CH3:17][NH2:18]>C(#N)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([NH:18][CH3:17])=[CH:11][N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 855929321-(6-Chloro-3-pyridylmethyl)amino-1-methylthio-2-nitroethylene

Product 1

HCID 43256191,1-Ethenediamine, N-[(6-chloro-3-pyridinyl)methyl]-N'-methyl-2-nitro-Yield 92.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.0 g of 1-(6-chloro-3-pyridylmethylamino)-1-methylthio-2-nitroethylene, 1.8 g of 40% aqueous methylamine solution and 20 ml of acetonitrile was refluxed for 3 hours and, then concentrated. The residue was washed with dichloromethane to give 1.73 g of 1-(6-chloro-3-pyridylmethylamino)-1-methylamino-2-nitroethylene. Mp 181°-183° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationconcentrated
  3. washThe residue was washed with dichloromethane

Sources & evidence

ORD record
ord-fb82296495ff4b458910120aaefba1b0
Source dataset
uspto-grants-1992_01
Patent number
US05084459

Reaction notes

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