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

HRID 868926ノート

反応式

HRID 868926 の反応式
[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

参加物

5

反応物 3

HCID 1049PyridineHCID 6259Phenacyl bromideHCID 2733398Ethyl thiooxamate

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-d5b116bca10b41a5ab760bd00d68d1a6
出典データセット
uspto-grants-2015_03
特許番号
US08969349B2

反応ノート

読み込み中…