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

HRID 1983134Notes

Reaction equation

HRID 1983134 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:26]2[CH2:31][CH2:30][S:29][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.[OH:32]OS([O-])=O.[K+].S(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:26]2[CH2:31][CH2:30][S:29](=[O:32])[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

Participants

8

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 sulfite

Product 1

HCID 167228524-{3-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenyl}-thiomorpholine 1-oxideYield 15%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

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 (660 mg, 1.52 mmol) in dichloromethane (7 mL), methanol (7 mL) and water (0.1 mL) was added oxone (1.87 g, 3.04 mmol) and stirred for 8 h at 60° C. The reaction mixture was cooled to ambient temperature and aqueous sodium bisulfite (38%, 5 mL) was added and stirred for 1 h. After the addition of aqueous sodium carbonate (saturated, 30 mL) the mixture was extracted with dichloromethane (30 mL) and washed with aqueous sodium carbonate (half-saturated, 30 mL). Drying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane:methanol=40:40:20:0 to 0:75:20:5) afforded the title compound (102 mg, 15%) as an off-white solid. MS: m/e=451.1 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. stirringstirred for 1 h
  3. extractionwas extracted with dichloromethane (30 mL)
  4. washwashed with aqueous sodium carbonate (half-saturated, 30 mL)
  5. dry with materialDrying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane:methanol=40:40:20:0 to 0:75:20:5)

Sources & evidence

ORD record
ord-519a25e8541e4fb4b9436dce27030fa6
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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