2-Acetyl-5-chlorothiophene → HCID 13411282、化合物

HRID 409025ノート

反応式

HRID 409025 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7](=O)[CH3:8])=[CH:4][CH:3]=1.Cl.[NH2:11][OH:12].C([O-])(=O)C.[Na+]>C(O)C.O>[Cl:1][C:2]1[S:6][C:5](/[C:7](=[N:11]/[OH:12])/[CH3:8])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 805722-Acetyl-5-chlorothiopheneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

生成物 1

HCID 13411282HCID 13411282、化合物

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

Combined 1-(5-chlorothiophen-2-yl)ethanone (100 g, 622 mmol), hydroxylamine hydrochloride (47.6 g, 685 mmol, 1.1 eq) and sodium acetate (56.2 g, 685 mmol, 1.1 eq) in 1 L of ethanol and 300 mL of water. The reaction was heated to reflux. After 3 h, the reaction was cooled to rt and concentrated. The residue was slurried in 500 mL of water overnight, filtered and dried to afford the crude solid. Purified by extraction of the solid with hot dichloromethane, cooling to rt and filtering to remove unreacted starting material. The solid was slurried in hot dichloromethane several times to extract the solid enriched in the first eluting (E-oxime) compound (100% DCM) after concentration. The highly crystalline material was purified by column chromatography using 100% dichloromethane to afford (E)-1-(5-chlorothiophen-2-yl)ethanone oxime. NMR (400 MHz, DMSO-d6) δ 11.31 (s, 1H), 7.21 (d, J=3.9 Hz, 1H), 7.07 (d, J=3.9 Hz, 1H), 2.12 (s, 3H) ppm.

後処理

  1. temperatureThe reaction was heated to reflux
  2. concentrationconcentrated
  3. waitThe residue was slurried in 500 mL of water overnight
  4. filtrationfiltered
  5. customdried
  6. customto afford the crude solid
  7. customPurified by extraction of the solid with hot dichloromethane
  8. temperaturecooling to rt
  9. filtrationfiltering
  10. customto remove unreacted
  11. extractionto extract the solid
  12. washfirst eluting (E-oxime) compound (100% DCM)
  13. concentrationafter concentration
  14. customThe highly crystalline material was purified by column chromatography

出典と根拠

ORDレコード
ord-3de2de1ef60f47eea71596b36d6ac44e
出典データセット
uspto-grants-2014_06
特許番号
US08759371B2

反応ノート

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