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

HRID 249508Notes

Reaction equation

HRID 249508 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]>CCO>[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 53.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 100 ml of EtOH was dissolved 1.2 g (4.6×10-3 mole) of 1-(6-chloro-3-pyridylmethyl)amino-1-methylthio-2-nitroethylene and on reflux, a solution of 0.84 g of 40% aqueous methylamine in 30 ml EtOH was added dropwise over 1 hour. After cooling, the reaction mixture was concentrated under reduced pressure to about 50 ml and the resulting crystals were collected by filtration and dried to give 0.6 g of the title compound as pale yellow needles.

Workup

  1. temperatureon reflux
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure to about 50 ml
  4. filtrationthe resulting crystals were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-659fbe34b189419289ea8e87ff3e23ac
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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