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

HRID 1925212ノート

反応式

HRID 1925212 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
135 °C

実験手順

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].

後処理

  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.

出典と根拠

ORDレコード
ord-4318b618e5674f148c29af60b037923d
出典データセット
uspto-grants-2012_05
特許番号
US08178672B2

反応ノート

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