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

HRID 1954986Notes

Reaction equation

HRID 1954986 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 orsder, 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 orsder
  7. customdried

Sources & evidence

ORD record
ord-f0ea06bdaade441381b1151829b5a9bc
Source dataset
uspto-grants-2000_09
Patent number
US06124297

Reaction notes

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