Sodium Carbonate → 4-{3-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenyl}-thiomorpholine 1,1-dioxide

HRID 1983108노트

반응식

HRID 1983108 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:26]2[CH2:31][CH2:30]S[CH2:28][CH2:27]2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]([C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[N:12][N:13]=1.O[O:33][S:34]([O-:36])=O.[K+].S(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:26]2[CH2:31][CH2:30][S:34](=[O:36])(=[O:33])[CH2:28][CH2:27]2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]([C:14]2[C:15]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:16][O:17][C:18]=2[CH3:19])=[N:12][N:13]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 167226464-{3-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenyl}-thiomorpholineHCID 23665763Sodium BisulfiteHCID 23707502Potassium hydroxy sulfite2회

생성물 1

HCID 167226944-{3-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenyl}-thiomorpholine 1,1-dioxide수율 69.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-{3-methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenyl}-thiomorpholine (156 mg, 0.36 mmol) in dichloromethane (2 mL) and methanol (2 mL) was added oxone (331 mg, 0.54 mmol) and the reaction mixture was stirred for 18 h at ambient temperature and then for 4 h at 50° C. After cooling to ambient temperature oxone (331 mg, 0.54 mmol) was added and stirred for 18 h at 50° C. before it was cooled to ambient temperature and sodium bisulfite solution (38%, 1.5 mL) was added and stirred for 15 min. After the addition of aqueous sodium carbonate (saturated, 10 mL) the mixture was extracted with ethyl acetate (20 mL) and washed with aqueous sodium carbonate (20 mL). After drying over sodium sulfate the concentrated residue was dissolved in dichloromethane (5 mL) and diluted with tert-butylmethylether (20 mL). The dichloromethane was distilled off and the resulting suspension was filtered affording the title compound (116 mg, 69%) as a white solid. MS: m/e=467.2 [M+H]+.

후처리

  1. waitfor 4 h at 50° C
  2. additionwas added
  3. stirringstirred for 18 h at 50° C. before it
  4. temperaturewas cooled to ambient temperature
  5. stirringstirred for 15 min
  6. extractionwas extracted with ethyl acetate (20 mL)
  7. washwashed with aqueous sodium carbonate (20 mL)
  8. dry with materialAfter drying over sodium sulfate the concentrated residue
  9. dissolutionwas dissolved in dichloromethane (5 mL)
  10. additiondiluted with tert-butylmethylether (20 mL)
  11. distillationThe dichloromethane was distilled off
  12. filtrationthe resulting suspension was filtered

출처 및 근거

ORD 기록
ord-24158748fdb74b12977bbb2891de7025
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07541372B2

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