Ethanol → 4-Amino-5-(4-hydroxy-phenylsulfanyl)-thiophene-2-carboxylic acid (3-bromo-phenyl)-amide

HRID 605314Notes

Reaction equation

HRID 605314 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[S:12][C:13]([S:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[C:14]([N+:16]([O-])=O)[CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+].O.C(O)C>O1CCCC1.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[S:12][C:13]([S:19][C:20]3[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=3)=[C:14]([NH2:16])[CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 670409995-(4-Hydroxy-phenylsulfanyl)-4-nitro-thiophene-2-carboxylic acid (3-bromo-phenyl)-amide

Product 1

HCID 670406504-Amino-5-(4-hydroxy-phenylsulfanyl)-thiophene-2-carboxylic acid (3-bromo-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 351D (1 equiv), iron powder (5 equiv) and ammonium chloride (3 equiv) in a mixture of tetrahydrofuran, water and ethanol was heated to reflux for 3 hours. The mixture was cooled to room temperature, filtered through a pad of celite, which was washed with ethanol and the resultant filtrate concentrated under vacuum. The material was then dissolved in water and extracted with ethyl acetate, the organic layer dried and concentrated under vacuum to provide the title product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered through a pad of celite, which
  4. washwas washed with ethanol
  5. concentrationthe resultant filtrate concentrated under vacuum
  6. dissolutionThe material was then dissolved in water
  7. extractionextracted with ethyl acetate
  8. customthe organic layer dried
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0361d5052b0649b5a41e21c17847411b
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…