Sodium Hydroxide → 2-[N-(2,4,6-trifluorophenyl)sulfamoyl] acetic acid

HRID 654007

Reaction equation

HRID 654007 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][S:5](=[O:17])(=[O:16])[NH:6][C:7]1[C:12]([F:13])=[CH:11][C:10]([F:14])=[CH:9][C:8]=1[F:15].[OH-].[Na+]>O1CCOCC1>[F:15][C:8]1[CH:9]=[C:10]([F:14])[CH:11]=[C:12]([F:13])[C:7]=1[NH:6][S:5]([CH2:4][C:3]([OH:18])=[O:2])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 150576002-[N-(2,4,6-trifluorophenyl)sulfamoyl]-acetic acid methyl ester

Product 1

HCID 150576012-[N-(2,4,6-trifluorophenyl)sulfamoyl] acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.37 g (4.8 mmol) of 2-[N-(2,4,6-trifluorophenyl)sulfamoyl]-acetic acid methyl ester is dissolved in 15 ml of dioxane, 7.5 ml of 2N sodium hydroxide solution is added and it is stirred for one hour at room temperature. The solution is then evaporated to dryness, the residue is dissolved in water, the solution is acidified with 2N hydrochloric acid and extracted twice with ethyl acetate. The ethyl acetate extract is dried on magnesium sulfate, filtered and evaporated to dryness. The residue is crystallized from diethyl ether. 1.12 g (4.16 mmol)=86.68% of the theoretical yield is obtained. Melting point 126-127° C.

Workup

  1. customThe solution is then evaporated to dryness
  2. dissolutionthe residue is dissolved in water
  3. extractionextracted twice with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. customis dried on magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue is crystallized from diethyl ether
  9. custom1.12 g (4.16 mmol)=86.68% of the theoretical yield
  10. customis obtained

Sources & evidence

ORD record
ord-7068af3026e04935ba61ca13c7ac8a53
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Linked notes

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