Ammonia → HCID 59896634, compound

HRID 1682232Notes

Reaction equation

HRID 1682232 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-43763fe5249e4150af10b5b142f092ee
Source dataset
uspto-grants-1992_12
Patent number
US05175301

Reaction notes

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