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

HRID 1925212노트

반응식

HRID 1925212 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
135 °C

실험 절차

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].

후처리

  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.

출처 및 근거

ORD 기록
ord-4318b618e5674f148c29af60b037923d
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178672B2

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