Ethanol → Ethyl 2-benzylthiazole-4-carboxylate

HRID 615919

반응식

HRID 615919 반응식
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:10]1([CH2:16][C:17]([NH2:19])=[S:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)C>N1C=CC=CC=1>[CH2:16]([C:17]1[S:18][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:19]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 66144Ethyl bromopyruvateHCID 7313682-Phenylethanethioamide

생성물 1

HCID 1491568Ethyl 2-benzylthiazole-4-carboxylate수율 45.6%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

40 g of ethyl bromopyruvate were progressively added to a mixture of 30.2 g of phenylthioacetamide, 120 ml of ethanol and 20 ml of pyridine and the mixture was refluxed for 16 hours. The mixture was evaporated to dryness under reduced pressure and the residue was added to a water-ether mixture. The mixture was stirred and the decanted aqueous phase was extracted with ether. The combined organic phases were evaporated to dryness and the residue was chromatographed over silica gel. Elution with a 7-3 hexane-ethyl acetate mixture yielded 22.5 g of ethyl 2-benzyl-thiazole-4-carboxylate melting at 78°-79° C.

후처리

  1. temperaturethe mixture was refluxed for 16 hours
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. additionthe residue was added to a water-ether mixture
  4. extractionthe decanted aqueous phase was extracted with ether
  5. customThe combined organic phases were evaporated to dryness
  6. customthe residue was chromatographed over silica gel
  7. washElution with a 7-3 hexane-ethyl acetate mixture

출처 및 근거

ORD 기록
ord-6e2c49df7d8d4595b97744a178310842
출처 데이터셋
uspto-grants-1985_02
특허 번호
US04501894

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