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Sodium Acetate → Ethyl 5-ethyl-1H-imidazole-2-carboxylate

HRID 43430
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HRID 43430 반응식
C([O-])(=O)C.[Na+].Cl.[NH2:7][CH2:8][C:9](=O)[CH2:10][CH3:11].F[B-](F)(F)F.[NH:18]=[C:19](SC)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)(=O)C>[CH2:10]([C:9]1[NH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:7][CH:8]=1)[CH3:11]
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참가 물질

5

반응물 3

HCID 517045Sodium AcetateHCID 116079121-aminobutan-2-one HydrochlorideHCID 86648451Ethyl imino(methylthio)acetate tetrafluoroborate

생성물 1

HCID 14990237Ethyl 5-ethyl-1H-imidazole-2-carboxylate수율 72.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

Sodium acetate (9.3 g, 113.4 mmol) was added to a solution of 1-amino-butan-2-one hydrochloride (3.41 g, 27.60 mmol) and ethyl imino(methylthio)acetate tetrafluoroborate (7.45 g, 31.84 mmol) synthesized according to the method described in the document (J. Med. Chem., 38, 1995, 2196-2201) in acetic acid (120 mL), and the mixture was stirred at 100° C. for four hours. The reaction solution was concentrated under reduced pressure and then saturated aqueous sodium bicarbonate solution was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with brine and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1, 2/1, 1/2) to obtain 3.35 g of the title compound as a pale yellow solid (72%).

후처리

  1. customsynthesized
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionsaturated aqueous sodium bicarbonate solution was added to the reaction solution
  4. extractionfollowed by extraction with ethyl acetate
  5. washThen, the organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentration under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1, 2/1, 1/2)

출처 및 근거

ORD 기록
ord-6a923d14fb724dcb8fcb490c151050da
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08536197B2

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