Sodium Hydroxide → 4-(1-Ethyl-5-trifluoromethanesulfonyl-1H-benzoimidazol-2-yl)-benzoic acid

HRID 1358762

Reaktionsgleichung

Reaktionsgleichung von HRID 1358762
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH3:16])[C:13]3[CH:17]=[CH:18][C:19]([S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])=[CH:20][C:12]=3[N:11]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>C(O)C>[CH2:15]([N:14]1[C:13]2[CH:17]=[CH:18][C:19]([S:21]([C:24]([F:26])([F:25])[F:27])(=[O:22])=[O:23])=[CH:20][C:12]=2[N:11]=[C:10]1[C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:28])=[O:2])=[CH:9][CH:8]=1)[CH3:16]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 99534764-(1-Ethyl-5-trifluoromethanesulfonyl-1H-benzoimidazol-2-yl)-benzoic acid methyl ester

Produkt 1

HCID 99088214-(1-Ethyl-5-trifluoromethanesulfonyl-1H-benzoimidazol-2-yl)-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-(1-Ethyl-5-trifluoromethanesulfonyl-1H-benzoimidazol-2-yl)-benzoic acid methyl ester (152 mg, 0.368 mmol) was dissolved in warm ethanol (7 mL) and 1 M sodium hydroxide (1.0 mL) was added. The reaction mixture was heated to near reflux and stirred for 3 h. The reaction mixture was then partially evaporated by blowing with a stream of nitrogen and transferred to a vial containing EtOAc and 1 M aqueous hydrochloric acid. The organic phase was separated, washed with saturated brine, dried (Na2SO4) and evaporated to yield the acid 36: 1HNMR (400 MHz, d6-DMSO) δ 8.47 (d, J=1.55 Hz, 1H), 8.18 (d, J=8.66 Hz, 1H), 8.15 (d, J=8.81 Hz, 2H), 8.01 (dd, J=7.17, 1.17 Hz, 1H), 7.95 (d, J=8.25 Hz, 2H), 4.45 (q, J=7.11 Hz, 2H), 1.37 (t, J=7.09 Hz, 3H); LCMS-APCI m/z 397 [M−1]−.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto near reflux
  3. customThe reaction mixture was then partially evaporated
  4. additiona vial containing EtOAc and 1 M aqueous hydrochloric acid
  5. customThe organic phase was separated
  6. washwashed with saturated brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-92b85b150bbc4a138a03ffdc6e1a5ecc
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596772B1

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