Water → 3-Amino-N-(3-bromo-phenyl)-4-(3-hydroxy-phenylsulfanyl)-benzamide

HRID 605124Notes

Reaction equation

HRID 605124 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:27])[C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=3)=[C:12]([N+:24]([O-])=O)[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+].O1CCCC1.O>C(O)C.[Fe]>[NH2:24][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[S:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=1)[C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[O:27]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 67040801N-(3-Bromo-phenyl)-4-(3-hydroxy-phenylsulfanyl)-3-nitro-benzamide

Product 1

HCID 670401443-Amino-N-(3-bromo-phenyl)-4-(3-hydroxy-phenylsulfanyl)-benzamideYield 101.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

A solution of the product of Example 79A (0.43 g, 0.97 mmol), iron powder (0.28 g, 5.0 mmol) and ammonium chloride (0.08 g, 1.5 mmol) in an ethanol (18 mL), tetrahydrofuran (18 mL), and water (6 mL) solution was heated to reflux for 3 hours. The resultant mixture was diluted with ethanol (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 dried over sodium sulfate, filtered and concentrated under vacuum to provide the title compound (0.41 g, 98%).

Workup

  1. temperatureto reflux for 3 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. dry with materialThe combined extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9b8bc476cbe341e29e723bbcc0abcce3
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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