Water → N-[4-(2-Amino-4-hydroxy-phenylsulfanyl)-phenyl]-acetamide

HRID 883912Notes

Reaction equation

HRID 883912 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=2)=[C:4]([N+:19]([O-])=O)[CH:3]=1.[Cl-].[NH4+].C1COCC1.O>CO.[Fe]>[NH2:19][C:4]1[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][C:5]=1[S:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 67249335N-[4-(4-Hydroxy-2-nitro-phenylsulfanyl)-phenyl]-acetamide

Product 1

HCID 67250701N-[4-(2-Amino-4-hydroxy-phenylsulfanyl)-phenyl]-acetamideYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent2×

Procedure

A solution of the product of Example 38a (2.7 g, 8.97 mmol), iron powder (2.0 g, 35.9 mmol) and ammonium chloride (0.58 g, 10.76 mmol) in a methanol (6 mL), THF (6 mL), and water (2 mL) solution was heated to reflux for 1.5 hours. The resultant mixture was diluted with methanol (50 mL) and filtered through a pad of celite. The filtrate was concentrated under vacuum to a volume of 10 mL, the solution diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined extracts were washed with 10% sodium chloride then dried over magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (2.46 g, 77%).

Workup

  1. temperatureto reflux for 1.5 hours
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated under vacuum to a volume of 10 mL
  4. additionthe solution diluted with water (50 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. washThe combined extracts were washed with 10% sodium chloride
  7. dry with materialthen dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dc32c56c0f994520a90b5282084e6252
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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