Sodium disulfide → 3-(3-Phenyl-1-propenyl)aniline

HRID 1903651Notes

Reaction equation

HRID 1903651 reaction equation
[C:1]1([CH2:7][CH:8]=[CH:9][C:10]2[CH:11]=[C:12]([N+:16]([O-])=O)[CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.N.[S-][S-].[Na+].[Na+]>C(O)C>[C:1]1([CH2:7][CH:8]=[CH:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[NH2:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 89870Sodium disulfideHCID 12896473Azane;hydrateHCID 538829723-(3-Phenyl-1-propenyl)nitrobenzene

Product 1

HCID 540429893-(3-Phenyl-1-propenyl)anilineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(3-phenyl-1-propenyl)nitrobenzene (10.5 g) in 200 ml of ethanol were added 70 ml of 35% ammonia water and 44 g of sodium disulfide. After heating under reflux for 2 hours, the solvent was removed under reduced pressure, followed by extraction with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure to give 7.8 g of 3-(3-phenyl-1-propenyl)aniline (yield, 85%). B.P. 128°-130° C./0.09 mmHg.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 2 hours
  3. customthe solvent was removed under reduced pressure
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-0fca6851e60a46b480237d921ebc77b7
Source dataset
uspto-grants-1984_03
Patent number
US04437880

Reaction notes

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