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

HRID 1682222Notes

Reaction equation

HRID 1682222 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-36b2c5ae3490455bb2dafc5100a48a4c
Source dataset
uspto-grants-1992_12
Patent number
US05175301

Reaction notes

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