Methylamine → N~1~-[(4-Chlorophenyl)methyl]-N'~1~-methyl-2-nitroethene-1,1-diamine

HRID 249519Notes

Reaction equation

HRID 249519 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](SC)=[CH:9][N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[CH3:17][NH2:18]>CCO>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8]([NH:18][CH3:17])=[CH:9][N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 70157188HCID 70157188, compound

Product 1

HCID 59896578N~1~-[(4-Chlorophenyl)methyl]-N'~1~-methyl-2-nitroethene-1,1-diamineYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 100 ml of EtOH on reflux was dissolved 2.59 g (0.01 mole) of 1-(4-chlorobenzyl)amino-1-methylthio-2-nitroethylene, and with refluxing continued, a solution of 1.94 g of 40% aqueous methylamine solution in 10 ml of EtOH was added dropwise over a period of 50 minutes. After completion of dropwise addition, the mixture was further refluxed for 15 minutes, at the end of which time it was cooled with ice-water, whereupon crystals separated out. The crystals were collected by filtration, washed with EtOH and ether in that order, and dried. The procedure gave 1.66 g of the title compound as white crystals.

Workup

  1. temperaturewith refluxing
  2. additionAfter completion of dropwise addition
  3. temperaturethe mixture was further refluxed for 15 minutes, at the end of which time it
  4. customseparated out
  5. filtrationThe crystals were collected by filtration
  6. washwashed with EtOH and ether in that order
  7. customdried

Sources & evidence

ORD record
ord-88b4ddfcf1bf404f9916189725e4ac3b
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

Loading…