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

HRID 478772

반응식

HRID 478772 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-eacb283d896a40578f191fee9c296335
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642206B2

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