Ethanol → 2-Benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]-5-(2 methylthiazol-4-yl)benzamide

HRID 421062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421062
[CH2:1]([O:8][C:9]1[CH:31]=[CH:30][C:29]([C:32](=O)[CH2:33]Br)=[CH:28][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36]([NH2:39])(=[S:38])[CH3:37].C(=O)([O-])O.[Na+].C(O)C>O>[CH2:1]([O:8][C:9]1[CH:31]=[CH:30][C:29]([C:32]2[N:39]=[C:36]([CH3:37])[S:38][CH:33]=2)=[CH:28][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[C:18]([C:20]([F:22])([F:23])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:25])[F:26])[CH:15]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 516892Sodium Bicarbonate2×HCID 2723949ThioacetamideHCID 178603042-Benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)phenyl]benzamide

Produkt 1

HCID 178602912-Benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]-5-(2 methylthiazol-4-yl)benzamideAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)-phenyl]benzamide (280 mg, 0.5 mmol), thioacetamide (41 mg, 0.55 mmol), sodium hydrogen carbonate (50 mg, 0.6 mmol) and ethanol (15 mL) was refluxed for 1 hour. The reaction mixture was poured into water, neutralized by sodium hydrogen carbonate, and extracted with ethyl acetate. After the organic layer was washed with water and saturated brin, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (hexane:ethyl acetate=4:1) to give the title compound (181 mg, 67.5%) as a white solid.

Aufarbeitung

  1. temperaturewas refluxed for 1 hour
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with water
  4. dry with materialsaturated brin, dried over anhydrous magnesium sulfate
  5. customthe residue obtained by evaporation under reduced pressure
  6. customwas purified by chromatography on silica gel (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-cb85f438f16b46769c46cd95ed8e426b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097759B2

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