m-Chloroperbenzoic acid → HCID 86753583, 화합물

HRID 343086노트

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HRID 343086 반응식
[CH3:1][S:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1.OS([O-])=O.[Na+]>ClCCl>[CH3:1][S:2]([C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)=[O:32]

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 86753582HCID 86753582, 화합물

생성물 1

HCID 86753583HCID 86753583, 화합물수율 36.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a chilled solution (-78° C.) of 4-[5-methylthio-3-phenylisoxazol-4-yl]benzenesulfonamide (Example 58) (0.256 g, 0.814 mmol) in dichloromethane (8 mL) was added MCPBA (0.234 g of 60% reagent, 0.814 mmol). After 1 hour, the reaction was warmed to 0° C. and held there for an additional hour. Dichloromethane (30 mL) and a solution of NaHSO3 were added and mixed for 5 minutes. The resulting mixture was extracted with ethyl acetate (20 mL) and the layers separated. The organic phase was washed with NaHSO3 solution and with NaHCO3 solution, dried over MgSO4, filtered and concentrated in vacuo yielding 4-[5-methylsulfinyl-3-phenylisoxazol-4-yl]benzenesulfonamide (0.107 g, 36%) as a pale yellow powder: mp 194°-204° C. 1H NMR (CDCl3 with DMSO6 /300 MHz) 7.98 (d, 2H, 8.46 Hz), 7.53-7.37 (m, 7H), 6.39 (s, 2H), 3.18 (s, 3H). FABLRMS m/z 363 (M+H). FABHRMS m/z 363.0480 (M+H, C16H15N2O4S2 requires 363.0473). Anal. Calc'd for C16H14N2O4S2 : C, 53.03; H, 3.89; N, 7.73. Found: C, 53.24; H, 3.96; N, 7.50.

후처리

  1. waitheld there for an additional hour
  2. additionmixed for 5 minutes
  3. extractionThe resulting mixture was extracted with ethyl acetate (20 mL)
  4. customthe layers separated
  5. washThe organic phase was washed with NaHSO3 solution and with NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2cf96aed3e574ceea2d83d59be2b5b24
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859257

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