m-Chloroperbenzoic acid → HCID 86753583、化合物

HRID 343086ノート

反応式

HRID 343086 の反応式
[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]

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 86753582HCID 86753582、化合物

生成物 1

HCID 86753583HCID 86753583、化合物収率 36.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2cf96aed3e574ceea2d83d59be2b5b24
出典データセット
uspto-grants-1999_01
特許番号
US05859257

反応ノート

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