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

HRID 883934

Reaktionsgleichung

Reaktionsgleichung von HRID 883934
[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]

Komponenten

8

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3c8c4df34f194b7a97e86d8864920eac
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236950B2

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