Sodium Carbonate → HCID 16722752, compound

HRID 2421128Notes

Reaction equation

HRID 2421128 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:27][CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[N:15][N:14]=1.[OH:30]OS([O-])=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:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][S:27](=[O:30])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[N:15][N:14]=1

Participants

7

Reactant 4

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

Product 1

HCID 16722752HCID 16722752, compoundYield 20.2%

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 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 and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane:methanol=40:50:10:0 to 0:90:0:10) afforded the title compound (50 mg, 20%) as a white solid. MS: m/e=421.1 [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 and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane:methanol=40:50:10:0 to 0:90:0:10)

Sources & evidence

ORD record
ord-9c4bc725031f4fa08bc06381940b7b6f
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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