Sodium Acetate → {[2,6-Difluoro-4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]thio}methyl acetate

HRID 1838510노트

반응식

HRID 1838510 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:15][O:16][C:17]=2[CH3:18])[CH:5]=[C:6]([F:12])[C:7]=1[S:8]([CH3:11])(=O)=O.[C:25]([O-:28])(=[O:27])[CH3:26].[Na+]>C(OC(=O)C)(=O)C>[C:25]([O:28][CH2:11][S:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([C:13]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:15][O:16][C:17]=2[CH3:18])=[CH:5][C:6]=1[F:12])(=[O:27])[CH3:26]

참가 물질

4

반응물 2

HCID 517045Sodium AcetateHCID 99244894-[3,5-Difluoro-4-(methylsulfonyl)-phenyl]-5-methyl-3-phenylisoxazole

생성물 1

HCID 22746414{[2,6-Difluoro-4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]thio}methyl acetate수율 82.3%

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

A slurry of 4-[3,5-difluoro-4-(methylsulfinyl)phenyl]-5-methyl-3-phenylisoxazole (2.3 g, 6.8 mmol)(step 9 example 14), sodium acetate (3.4 g, 41 mmol) in acetic anhydride (30 mL) was heated and held at reflux for 9 hours. The mixture was concentrated on at reduced pressure and the residue was treated with dilute aqueous sodium bicarbonate and extracted with dichloromethane (1×200 mL, 2×75 mL). The combined extracts were washed with dilute sodium bicarbonate, dilute ammonium chloride, dried with magnesium sulfate and concentrated. The product was purified by silica gel chromatography using 1% ethyl acetate/50% dichloromethane in hexanes to give {[2,6-difluoro-4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]thio}methyl acetate as a white solid (2.1 g, 82%), MP 130.3-130.3° C. 1HNMR (CDCl3/400 MHz) 7.34-7.43 (m, 5H), 6.73-6.79 (m, 2H), 5.29 (s, 2H), 2.49 (s, 3H) 2.05 (s, 3H). HRMS m/z 376.0822 (M+H+, Calcd 376.0819). Anal. Calcd for C19H15F2NO3S: C, 60.79; H, 4.03; N, 3.73; Found: C, 60.44; H, 4.09, N 3.66.

후처리

  1. temperatureat reflux for 9 hours
  2. concentrationThe mixture was concentrated on at reduced pressure
  3. additionthe residue was treated with dilute aqueous sodium bicarbonate
  4. extractionextracted with dichloromethane (1×200 mL, 2×75 mL)
  5. washThe combined extracts were washed with dilute sodium bicarbonate, dilute ammonium chloride
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. customThe product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-2daab4f95a6745d8b77888f2c906f70e
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06673818B2

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