Pyridine → Ethyl 4-phenyl-1,3-thiazole-2-carboxylate

HRID 868926노트

반응식

HRID 868926 반응식
[NH2:1][C:2](=[S:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].N1C=CC=CC=1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O>C(O)C>[C:19]1([C:17]2[N:1]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:8][CH:16]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 6259Phenacyl bromideHCID 2733398Ethyl thiooxamate

생성물 1

HCID 24730326Ethyl 4-phenyl-1,3-thiazole-2-carboxylate수율 75.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To ethyl 2-amino-2-thioxoacetate (4 g, 30 mmol) in ethanol (50 mL) was added pyridine (0.24 g, 3 mmol). 2-Bromo-1-phenylethanone (5 g, 25 mmol) was added after 10 minutes and the mixture was then heated at reflux for 6 hours. The resulting mixture was washed with water and extracted with EtOAc and dried over anhydrous sodium sulfate. The solution was then concentrated under vacuum to give a crude product, which was purified by column chromatography to afford the title compound as a white solid (4.4 g). MS (ESI) m/z 233 (M+H+).

후처리

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 6 hours
  3. washThe resulting mixture was washed with water
  4. extractionextracted with EtOAc
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solution was then concentrated under vacuum
  7. customto give a crude product, which
  8. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-d5b116bca10b41a5ab760bd00d68d1a6
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969349B2

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