Sodium Hydroxide → HCID 15057597, compound

HRID 654005Notes

Reaction equation

HRID 654005 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][S:5](=[O:16])(=[O:15])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[F:14].[OH-].[Na+]>O1CCOCC1>[F:14][C:8]1[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=1[NH:6][S:5]([CH2:4][C:3]([OH:17])=[O:2])(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15057596HCID 15057596, compound

Product 1

HCID 15057597HCID 15057597, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.68 g (10.1 mmol) of 2-[N-(2,4-difluorophenyl)sulfamoyl]-acetic acid methyl ester is dissolved in 30 ml of dioxane, 15 ml of 2N sodium hydroxide solution is added and stirred for 30 minutes at room temperature. The reaction solution is then evaporated to dryness, the residue is dissolved in some water, the solution is again concentrated by evaporation, the residue is dissolved in 30 ml of water, acidified with 2N hydrochloric acid and the product is extracted with ethyl acetate. The organic phase is dried on sodium sulfate, filtered and evaporated to dryness in a vacuum The crude product is recrystallized from ether/hexane 1:1. 1.55 g (6.17 mmol)=61.1% of the theoretical yield is obtained as a crystallizate, melting point 110-111.5° C.

Workup

  1. customThe reaction solution is then evaporated to dryness
  2. dissolutionthe residue is dissolved in some water
  3. concentrationthe solution is again concentrated by evaporation
  4. dissolutionthe residue is dissolved in 30 ml of water
  5. extractionthe product is extracted with ethyl acetate
  6. customThe organic phase is dried on sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness in a vacuum The crude product
  9. customis recrystallized from ether/hexane 1:1
  10. custom1.55 g (6.17 mmol)=61.1% of the theoretical yield
  11. customis obtained as a crystallizate, melting point 110-111.5° C.

Sources & evidence

ORD record
ord-2f138af6b8c1424e9e217b01c9080bbc
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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