Dimethylamine → HCID 59896602, compound

HRID 249520Notes

Reaction equation

HRID 249520 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][NH:18][CH3:19]>CCO>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8]([N:18]([CH3:19])[CH3:17])=[CH:9][N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 70157188HCID 70157188, compound

Product 1

HCID 59896602HCID 59896602, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 100 ml of EtOH was dissolved 2.59 g (0.01 mole) of 1-(4-chlorobenzyl)amino-1-methylthio-2-nitroethylene with heating. Then, with refluxing and stirring, a solution of 2.25 g of 50% aqueous dimethylamine solution in 10 ml of EtOH was added dropwise over a period of 35 minutes. After completion of dropwise addition, the mixture was further stirred and refluxed for 2.5 hours. The solvent was then distilled off and the residue was diluted with ether and triturated, whereupon crystals separated. After addition of EtOH and ether (about 1:5), the crystals were collected by filtration, washed with ether and dried. The procedure gave 1.21 g of the title compound as white crystals.

Workup

  1. temperaturewith heating
  2. temperatureThen, with refluxing
  3. additionAfter completion of dropwise addition
  4. stirringthe mixture was further stirred
  5. temperaturerefluxed for 2.5 hours
  6. distillationThe solvent was then distilled off
  7. additionthe residue was diluted with ether
  8. customtriturated, whereupon crystals
  9. customseparated
  10. additionAfter addition of EtOH and ether (about 1:5)
  11. filtrationthe crystals were collected by filtration
  12. washwashed with ether
  13. customdried

Sources & evidence

ORD record
ord-6086163ae1c341f699bad148cf8df826
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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