Ammonium Chloride → HCID 14771321, compound

HRID 476737Notes

Reaction equation

HRID 476737 reaction equation
[CH:1]1([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+]>[Fe].O>[CH:1]1([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 12646352HCID 12646352, compound

Product 1

HCID 14771321HCID 14771321, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 8.5 g of 2-(cyclohexylthio)nitrobenzene, 9.6 g of iron powder, 0.61 g of ammonium chloride and 22 ml of water was stirred on heating at 90° C. for 3 hours. The temperature of the reaction solution was returned to room temperature, the reaction solution was filtered by Selite and extracted with dichloromethane. The dichloromethane layer was washed, in turn, with water and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated to give 7.3 g of 2-(cyclohexylthio)aniline as a yellow oil.

Workup

  1. customwas returned to room temperature
  2. filtrationthe reaction solution was filtered by Selite
  3. extractionextracted with dichloromethane
  4. washThe dichloromethane layer was washed, in turn, with water
  5. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1bfcd98e6ba94e46afa56b2a32beb6b0
Source dataset
uspto-grants-1989_12
Patent number
US04885367

Reaction notes

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