Ethanol → Diethyl 1H-imidazole-4,5-dicarboxylate

HRID 478772

反応式

HRID 478772 の反応式
[NH:1]1[C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:9]([OH:11])=[O:10])[N:3]=[CH:2]1.[CH2:12](N(CC)CC)[CH3:13].[CH2:19](O)[CH3:20]>ClCCl>[NH:1]1[C:5]([C:6]([O:8][CH2:12][CH3:13])=[O:7])=[C:4]([C:9]([O:11][CH2:19][CH3:20])=[O:10])[N:3]=[CH:2]1

参加物

5

反応物 3

HCID 702EthanolHCID 8471TriethylamineHCID 684421H-Imidazole-4,5-dicarboxylic acid

生成物 1

HCID 350670Diethyl 1H-imidazole-4,5-dicarboxylate収率 52%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Imidazole-4,5-dicarboxylic acid (7.55 g, 50.0 mmol) is dissolved in absolute ethyl alcohol (120 mL). The solution was cooled in an ice bath to 0° C. and bubbled dry HCl gas for 1 h. Later, the reaction mixture was refluxed at 80° C. for 7 h during which time all the starting material was consumed. The solvent was removed and the residue that obtained was dissolved in dichloromethane (200 mL) and the organic layer was neutralized with triethylamine. The organic layer was washed with cold water (100 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give 5.50 g (52%) of white solid: mp 175-177° C.; 1H NMR (CDCl3) δ1.40 (t, 3H), 4.41 (m, 2H), 7.84 (1H, C2H) and 11.55 (br s, 1H, NH).

後処理

  1. custombubbled dry HCl gas for 1 h
  2. temperatureLater, the reaction mixture was refluxed at 80° C. for 7 h during which time all the starting material
  3. customwas consumed
  4. customThe solvent was removed
  5. customthe residue that obtained
  6. washThe organic layer was washed with cold water (100 mL) and brine (50 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-eacb283d896a40578f191fee9c296335
出典データセット
uspto-grants-2003_11
特許番号
US06642206B2

関連ノート

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