Ammonia → HCID 59896634, compound

HRID 249518Notes

Reaction equation

HRID 249518 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.CCO.[NH3:20]>C1COCC1>[NH2:20][C:8]([NH:7][CH2:6][C:5]1[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][CH:4]=1)=[CH:9][N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 702EthanolHCID 70157188HCID 70157188, compound

Product 1

HCID 59896634HCID 59896634, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 2.59 g (0.01 mole) of 1-(4-chlorobenzyl)amino-1-methylthio-2-nitroethylene were added 45 ml of EtOH, 10 ml of THF and 1.02 g of 25% aqueous ammonia and the mixture was stirred at an external temperature of 60° C. for 5.5 hours. During this period, 1.02 g each of 25% aqueous ammonia was added after 1, 2 and 3 hours of reaction. The reaction mixture was ice-cooled and stirred, whereupon crystals separated out. The crystals were collected by filtration, washed with EtOH and ether in that order, and dried. The procedure gave 1.11 g of the title compound as white crystals.

Workup

  1. waitDuring this period
  2. customafter 1, 2 and 3 hours of reaction
  3. temperaturecooled
  4. stirringstirred, whereupon crystals
  5. customseparated out
  6. filtrationThe crystals were collected by filtration
  7. washwashed with EtOH and ether in that order
  8. customdried

Sources & evidence

ORD record
ord-6e865ff668ab4fb29bb15c6a6c457e89
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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