Sodium Carbonate → HCID 16722751, compound

HRID 2421127Notes

Reaction equation

HRID 2421127 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[O:17][C:16]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28]S[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[N:15][N:14]=1.O[O:31][S:32]([O-:34])=O.[K+].S(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[O:17][C:16]([C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH2:25][CH2:26][S:32](=[O:34])(=[O:31])[CH2:28][CH2:29]3)=[CH:22][CH:23]=2)=[N:15][N:14]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 16722750HCID 16722750, compoundHCID 23665763Sodium BisulfiteHCID 23707502Potassium hydroxy sulfite2×

Product 1

HCID 16722751HCID 16722751, compoundYield 29.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 4-{4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenyl}-thiomorpholine (239 mg, 0.59 mmol) in methanol (2 mL) and water (0.5 mL) was added oxone (545 mg, 0.89 mmol) and stirred for 18 h at 60° C. and for 4 h at 50° C. After the reaction mixture was cooled to ambient temperature further oxone (331 mg, 0.54 mmol) was added and stirred for 18 h at 50° C. It was cooled to ambient temperature and aqueous sodium bisulfite (38%, 1.5 mL) was then 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 (saturated, 20 mL). Drying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane:methanol=40:50:10:0 to 0:90:0:10) afforded the title compound (75 mg, 29%) as a white solid. MS: m/e=437.2 [M+H]+.

Workup

  1. additionwas added
  2. stirringstirred for 18 h at 50° C
  3. temperatureIt was cooled to ambient temperature
  4. stirringstirred for 15 min
  5. extractionwas extracted with ethyl acetate (20 mL)
  6. washwashed with aqueous sodium carbonate (saturated, 20 mL)
  7. dry with materialDrying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane:methanol=40:50:10:0 to 0:90:0:10)

Sources & evidence

ORD record
ord-083a62b90d2b440e9fe3405cdc088f66
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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