Ammonium Chloride → HCID 57550300, compound

HRID 1642266Notes

Reaction equation

HRID 1642266 reaction equation
[Cl-].[NH4+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)([O-])=O>C(O)C.O.[Fe]>[N:16]1[CH:15]=[CH:14][C:13]([S:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH2:3])=[CH:18][CH:17]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 137910794-[(2-Nitrophenyl)sulfanyl]pyridine

Product 1

HCID 57550300HCID 57550300, compoundYield 81.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a refluxing mixture of iron powder (3.15 g, 56.82 mmol) and ammonium chloride (380 mg, 7.1 mmol) in ethanol (45 mL) and water (8 mL) was added 4-(2-nitrophenylsulfanyl)-pyridine (AMR01105, 2.4 g, 10.33 mmol) and the resulting mixture was stirred at reflux for 2 h. After removal of the solvent, the residue was diluted in aqueous sodium hydrogen carbonate (40 mL) and extracted with DCM (3×20 mL). The organic layer was dried (MgSO4), filtered and evaporated to give 2-(pyridin-4-ylsulfanyl)-phenylamine (1.7 g, 81%) as a yellow solid, mp 103-107° C., which was used in the next step without further purification.

Workup

  1. temperatureat reflux for 2 h
  2. customAfter removal of the solvent
  3. additionthe residue was diluted in aqueous sodium hydrogen carbonate (40 mL)
  4. extractionextracted with DCM (3×20 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-91037cca88ce4af99e5cf7ebe0d08823
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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