Ammonium Chloride → N-[4-Amino-5-(4-hydroxy-phenylsulfanyl)-2-methyl-phenyl]-2-phenyl-acetamide

HRID 605290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605290
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:10]([N+:26]([O-])=O)=[CH:11][C:12]([CH3:25])=[C:13]([NH:15][C:16](=[O:24])[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+]>O1CCCC1.CO.O.[Fe]>[NH2:26][C:10]1[C:9]([S:8][C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:14][C:13]([NH:15][C:16](=[O:24])[CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:12]([CH3:25])[CH:11]=1

Komponenten

7

Edukt 2

HCID 25517Ammonium ChlorideHCID 67041085N-[5-(4-Hydroxy-phenylsulfanyl)-2-methyl-4-nitro-phenyl]-2-phenyl-acetamide

Produkt 1

HCID 67040658N-[4-Amino-5-(4-hydroxy-phenylsulfanyl)-2-methyl-phenyl]-2-phenyl-acetamideAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product of Example 265B (0.282 g, 0.715 mmol), iron powder (0.160 g, 2.86 mmol, 4.0 eq), and ammonium chloride (0.0469 g, 0.858 mmol, 1.2 eq) in tetrahydrofuran (6 mL), methanol (6 mL) and water (2 mL) was heated under reflux for 1.5 h and then cooled to room temperature. The reaction mixture was then filtered through Celite and the Celite pad rinsed with methanol (50 mL). The filtrate was evaporated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and evaporated to provide an orange oil that was triturated with dichloromethane to provide the title compound as a yellow powder (0.246 g, 94%).

Aufarbeitung

  1. temperatureunder reflux for 1.5 h
  2. filtrationThe reaction mixture was then filtered through Celite
  3. washthe Celite pad rinsed with methanol (50 mL)
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe residue partitioned between ethyl acetate and water
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto provide an orange oil that
  10. customwas triturated with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-5ddf1344285c4c008c2004f3bb6a0324
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910595B2

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