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 2421118Notes

Reaction equation

HRID 2421118 reaction equation
[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

Participants

7

Reactant 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 sulfite2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-1255318c252143648b4367725e7cd052
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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