ethyl 2-bromo-3-oxo-3-phenylpropanoate → HCID 44384908、化合物

HRID 1530006ノート

反応式

HRID 1530006 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=[S:9])[NH2:8])=[CH:3][CH:2]=1.Br[CH:11]([C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[C:18]1([C:17]2[N:8]=[C:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[S:9][C:11]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

4

反応物 2

HCID 237819ethyl 2-bromo-3-oxo-3-phenylpropanoateHCID 27237884-Pyridinecarbothioamide

生成物 1

HCID 44384908HCID 44384908、化合物収率 57%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of pyridine-4-carbothioamide (2.9 g, 21 mmol) in ethanol (150 mL) was added ethyl 2-bromo-3-oxo-3-phenylpropanoate (5.9 g, 22 mmol), and the mixture was heated under reflux for 8 hr. The reaction solution was allowed to cool to room temperature, and the solid was collected by filtration, washed with diethyl ether, dried, suspended in ethyl acetate (250 mL), and washed with saturated aqueous sodium bicarbonate solution (150 mL×2). The combined aqueous layer was extracted with ethyl acetate (100 mL×2). The combined organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was washed with diethyl ether, and collected by filtration to give the title compound (3.7 g, 57%) as a colorless solid.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hr
  3. filtrationthe solid was collected by filtration
  4. washwashed with diethyl ether
  5. customdried
  6. washwashed with saturated aqueous sodium bicarbonate solution (150 mL×2)
  7. extractionThe combined aqueous layer was extracted with ethyl acetate (100 mL×2)
  8. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  9. filtrationthe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. washThe residue was washed with diethyl ether
  12. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-60ff47c929ca4ef1908c1cdce0bb0e14
出典データセット
uspto-grants-2015_07
特許番号
US09090601B2

反応ノート

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