Acetic Anhydride → 1-[6-(4-Fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone

HRID 1925212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1925212
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([CH:15]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16](=[O:18])[CH3:17])[CH:13]=[CH:12][O:11]3)=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 574336106-(4-Fluorophenyl)-imidazo[2,1-b]oxazole

Produkt 1

HCID 167264821-[6-(4-Fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanoneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

To a mixture of 6-(4-fluorophenyl)-imidazo[2,1-b]oxazole (2675 g, 13.23 mol) and acetic anhydride (6.35 l) is added 160 ml of concentrated sulfuric acid. The reaction mixture is heated at 135° C. for 1.5 hours, then cooled to 80° C. with an ice bath. The reaction mixture is slowly quenched with 12.5 l of water. The solids are stirred overnight, filtered and air-dried. The solids are again suspended in water (15 l), stirred overnight, filtered, and washed with water (4 l) and then with toluene (4 l). The solid is dried under vacuum at 60° C., to give 2771 g (86%) of a dark brown solid; M.p.=173° C.; 300 MHz 1H NMR (DMSO-d6) δ 8.25-8.19 (m, 2H), 7.75-7.68 (m, 2H), 7.35-7.25 (m, 2H), 2.15 (s, 3H). LCMS: 245 [M+H].

Aufarbeitung

  1. temperaturecooled to 80° C. with an ice bath
  2. customThe reaction mixture is slowly quenched with 12.5 l of water
  3. filtrationfiltered
  4. customair-dried
  5. stirringstirred overnight
  6. filtrationfiltered
  7. washwashed with water (4 l)
  8. customThe solid is dried under vacuum at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-4318b618e5674f148c29af60b037923d
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178672B2

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