Ethanol → Ethyl 2-benzylthiazole-4-carboxylate

HRID 615919

反応式

HRID 615919 の反応式
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

参加物

5

反応物 3

HCID 702EthanolHCID 66144Ethyl bromopyruvateHCID 7313682-Phenylethanethioamide

生成物 1

HCID 1491568Ethyl 2-benzylthiazole-4-carboxylate収率 45.6%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6e2c49df7d8d4595b97744a178310842
出典データセット
uspto-grants-1985_02
特許番号
US04501894

関連ノート

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