(2,6-Dichloropyridin-3-YL)methanamine → 1-(2,6-Dichloro-3-pyridylmethyl)amino-1-methylamino-2-nitroethylene

HRID 1457900Notes

Reaction equation

HRID 1457900 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1.[CH3:11][NH:12][CH:13](SC)[CH2:14][N+:15]([O-:17])=[O:16]>CCO>[Cl:1][C:2]1[C:7]([CH2:8][NH:9][C:13]([NH:12][CH3:11])=[CH:14][N+:15]([O-:17])=[O:16])=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1

Participants

4

Reactant 2

HCID 15477284(2,6-Dichloropyridin-3-YL)methanamineHCID 15788612N-Methyl-1-(methylsulfanyl)-2-nitroethan-1-amine

Product 1

HCID 598966091-(2,6-Dichloro-3-pyridylmethyl)amino-1-methylamino-2-nitroethyleneYield 27.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.2 g (0.007 mole) of (2,6-dichloro-3-pyridylmethyl)amine and 1 g (0.007 mole) of 1-methylamino-1-methylthio-2-nitroethane was refluxed in 50 ml of EtOH for 6 hours. After cooling, the reaction mixture was concentrated and the resulting crystals were collected by filtration, washed with CH2Cl2 and a small amount of EtOH in that order and dried. The procedure gave 0.53 g of the title compound as a white powder.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with CH2Cl2
  5. dry with materiala small amount of EtOH in that order and dried

Sources & evidence

ORD record
ord-0262b9ba754642c8aed6f63195a06b30
Source dataset
uspto-grants-1998_12
Patent number
US05849768

Reaction notes

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