Methylamine → 1-Methylamino-1-(3-pyridylmethyl)amino-2-nitroethylene

HRID 249505Notes

Reaction equation

HRID 249505 reaction equation
CS[C:3]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[CH:4][N+:5]([O-:7])=[O:6].[CH3:16][NH2:17]>CCO>[CH3:16][NH:17][C:3]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[CH:4][N+:5]([O-:7])=[O:6]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 70155832HCID 70155832, compound

Product 1

HCID 701581981-Methylamino-1-(3-pyridylmethyl)amino-2-nitroethyleneYield 76.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 50 ml of EtOH was dissolved 2.3 g (0.01 mole) of 1-methylthio-1-(3-pyridylmethyl)amino-2-nitroethylene with heating and, then, a solution of 1.2 g (0.015 mole) of 40% aqueous methylamine in 10 ml of EtOH was added dropwise over a period of 30 minutes while refluxing. The mixture was further refluxed for 2 hours, after which it was concentrated. The crystals were collected by filtration and recrystallized from acetonitrile to give 1.6 g of the title compound as white prisms.

Workup

  1. temperaturewith heating
  2. temperaturewhile refluxing
  3. temperatureThe mixture was further refluxed for 2 hours
  4. concentrationafter which it was concentrated
  5. filtrationThe crystals were collected by filtration
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-1455d139af564afea4701866a67bc140
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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