Potassium peroxymonosulphate → 4-[3,5-Difluoro-4-(methylsulfonyl)-phenyl]-5-methyl-3-phenylisoxazole

HRID 47652노트

반응식

HRID 47652 반응식
S([O-])(O[O-])(=O)=[O:2].[K+].[K+].[F:9][C:10]1[CH:11]=[C:12]([C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:13]=[C:14]([F:19])[C:15]=1[S:16]([CH3:18])=[O:17].O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O.[Mg+2]>O.CO.ClCCl>[F:19][C:14]1[CH:13]=[C:12]([C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:11]=[C:10]([F:9])[C:15]=1[S:16]([CH3:18])(=[O:2])=[O:17]

참가 물질

7

반응물 3

HCID 10313463Potassium peroxymonosulphate2회HCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)HCID 227456134-[3,5-Difluoro-4-(methylsulfinyl)phenyl]-5-methyl-3-phenylisoxazole

생성물 1

HCID 99244894-[3,5-Difluoro-4-(methylsulfonyl)-phenyl]-5-methyl-3-phenylisoxazole수율 93.5%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매2회HCID 6344Dichloromethane용매2회

실험 절차

Potassium peroxymonosulfate (0.25 g, 0.40 mmol) and water (7 mL) were added to a mixture of 4-[3,5-difluoro-4-(methyl-sulfinyl)phenyl]-5-methyl-3-phenylisoxazole (0.10 g, 0.30 mmol), dichloromethane (4 mL), and methanol (4 mL). The mixture was stirred for four days at room temperature. To the mixture was added magnesium monoperoxyphathalate hexahydrate (0.50 g, 0.80 mmol), dichloromethane (20 mL), methanol (10 mL). The mixture was stirred vigorously for 18 hours. To the mixture was added potassium peroxymonosulfate (0.35 g, 0.57 mmol), and the reaction continued for 18 hours. The mixture was poured into water and extracted with dichloromethane (4×75 mL). The combined extracts were dried with magnesium sulfate, concentrated, and the residue purified by silica gel chromatography using 30% ethyl acetate in hexanes. A white solid (98 mg, 93%) was obtained. MP 140.4-143.4° C. 1H NMR (CDCl3/400 MHz) 7.35-7.45 (m, 5H), 6.84 (d, 2H, J=9.4), 3.32 (s, 3H) 2.52 (s, 3H). ESHRMS m/z 350.0642 (M+H+, Calcd 350.0662).

후처리

  1. stirringThe mixture was stirred vigorously for 18 hours
  2. waitthe reaction continued for 18 hours
  3. extractionextracted with dichloromethane (4×75 mL)
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-7cbd6652612f4c55b07a8147385f28b2
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699884B2

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