2-Acetyl-5-chlorothiophene → HCID 13411282, 화합물

HRID 409025

반응식

HRID 409025 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 13411282HCID 13411282, 화합물

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3de2de1ef60f47eea71596b36d6ac44e
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759371B2

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