Water → {4-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 883988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883988
[Cl:1][C:2]([Cl:35])([Cl:34])[CH2:3][O:4][C:5](=[O:33])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:29])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[CH:16][C:15]=2[N+:30]([O-])=O)=[CH:9][CH:8]=1.[Cl-].[NH4+].O1CCCC1.O>C(O)C.[Fe]>[Cl:35][C:2]([Cl:1])([Cl:34])[CH2:3][O:4][C:5](=[O:33])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:29])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[CH:16][C:15]=2[NH2:30])=[CH:11][CH:12]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 67040283{4-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

Produkt 1

HCID 67040452{4-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl esterAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

The product from Example 88B (6.0 g, 10 mmol), iron powder (2.8 g, 50 mmol) and ammonium chloride (0.81 g, 15 mmol) in a mixture of ethanol (60 mL), tetrahydrofuran (60 mL), and water (20 mL) was heated under reflux for 5 hours and then cooled to room temperature. The reaction mixture was filtered through Celite and the filter pad was rinsed with ethanol (100 mL). The filtrate was evaporated under reduced pressure to leave a residue which was triturated with hexanes/ethyl acetate 4/1 to provide the title product (2.39 g, 42%) as a tan solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. washthe filter pad was rinsed with ethanol (100 mL)
  5. customThe filtrate was evaporated under reduced pressure
  6. customto leave a residue which
  7. customwas triturated with hexanes/ethyl acetate 4/1

Quellen und Nachweise

ORD-Eintrag
ord-bf5ebefbe48c40289fcc90c84646ac35
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236950B2

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