Water → {4-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenoxy]-phenyl}-carbamic acid tert-butyl ester

HRID 883934

Reaction equation

HRID 883934 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=3)=[CH:17][C:16]=2[N+:31]([O-])=O)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].O>C(O)C.O1CCCC1.C(OCC)(=O)C.[Fe]>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:24]=[CH:25][C:26]([Br:29])=[CH:27][CH:28]=3)=[CH:17][C:16]=2[NH2:31])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67040702{4-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenoxy]phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 67040083{4-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenoxy]-phenyl}-carbamic acid tert-butyl esterYield 96%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 49B (7.383 g, 13.97 mmol), iron powder (4.80 g, 85.94 mmol) and ammonium chloride (4.896 g, 91.53 mmol) in ethanol (60 mL), tetrahydrofuran (60 mL), and water (30 mL) was heated at 80° for 1.5 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate (300 mL) and washed with water (4×100 mL) and brine (50 mL). The organic phase was dried over sodium sulfate, filtered and concentrated under vacuum to provide the title compound as a light tan solid (6.658 g, 13.36 mmol, 96%).

Workup

  1. washwashed with water (4×100 mL) and brine (50 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3c8c4df34f194b7a97e86d8864920eac
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Linked notes

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