Lithium hydroxide, monohydrate → 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylic acid

HRID 75486ノート

反応式

HRID 75486 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[N:10]=[C:9]2[CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]=[C:9]2[CH2:18][CH2:19][CH3:20])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 54579226ethyl 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylate2 回

生成物 1

HCID 545792281-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylic acid収率 64%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
55 °C

実験手順

To a solution of ethyl 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylate (compound 5, 1.28 g, 4.37 mmol) in THF/water (20/20 mL) was added lithium hydroxide monohydrate at room temperature. The reaction mixture was stirred at 55° C. for 12 hrs. The mixture was washed with CH2Cl2, the aqueous layer was acidified with 1N-HCl solution (pH≈6), extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The obtained product was washed with hexane to provide the title compound (740 mg, 64%) as a pale brown solid.

後処理

  1. washThe mixture was washed with CH2Cl2
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe obtained product was washed with hexane

出典と根拠

ORDレコード
ord-ded33343f8484d0885807ce27b121196
出典データセット
uspto-grants-2014_09
特許番号
US08835436B2

反応ノート

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