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

HRID 883945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883945
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:27])[C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[C:12]([N+:24]([O-])=O)[CH:11]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.C(O)C.O.[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][C:20]([OH:23])=[CH:19][CH:18]=1)[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:27]

Komponenten

7

Edukt 2

HCID 10340Sodium CarbonateHCID 67040744N-(4-Bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-3-nitro-benzamide

Produkt 1

HCID 670402693-Amino-N-(4-bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-benzamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A suspension of the product of Example 53A (409.9 mg, 0.9205 mmol) and iron powder (206 mg, 3.682 mmol) in acetic acid (7 mL) and ethanol (7 mL) was heated at reflux under a nitrogen atmosphere for 1 hour. The reaction was cooled to room temperature. The mixture was diluted with water (30 mL), the pH adjusted to 6 with solid sodium carbonate, and the aqueous extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated under vacuum to provide the title compound as a tan solid (290 mg, 0.6983 mmol, 76%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 1 hour
  3. extractionthe aqueous extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic extracts were washed with brine (25 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fa6db86eb8be4f779b6ffd5bccd94cf4
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236950B2

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