Sodium Hydroxide → Mofezolac

HRID 847534Notes

Reaction equation

HRID 847534 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[C:14]([CH2:24][C:25]([O:27]C)=[O:26])[O:13][N:12]=2)=[CH:7][CH:6]=1>>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[C:14]([CH2:24][C:25]([OH:27])=[O:26])[O:13][N:12]=2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 109262505-Isoxazoleacetic acid, 3,4-bis(4-methoxyphenyl)-, methyl ester

Product 1

HCID 4237Mofezolac

Conditions

Temperature
40 °C

Procedure

To 15 ml of 2% aqueous solution of sodium hydroxide was added 1.77 g of methyl [3,4-bis(4-methoxyphenyl)isoxazol-5-yl]acetate obtained in Reference Example 1 and the mixture was stirred at 40° C. over night. After completion of the reaction, the reaction mixture was washed with ether twice, and thereto was added 5 ml of 10% HCl while cooling with ice. The mixture was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The organic layer was concentrated at a reduced pressure, giving the above-identified compound as white solid.

Workup

  1. customobtained in Reference Example 1
  2. customAfter completion of the reaction
  3. washthe reaction mixture was washed with ether twice
  4. additionwas added 5 ml of 10% HCl
  5. temperaturewhile cooling with ice
  6. extractionThe mixture was extracted with ethyl acetate
  7. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe organic layer was concentrated at a reduced pressure

Sources & evidence

ORD record
ord-52e6f04465654535935392706e7485aa
Source dataset
uspto-grants-1992_08
Patent number
US05142091

Reaction notes

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