Hydrochloric Acid → 2-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]acetic acid

HRID 248756

Reaction equation

HRID 248756 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][S:5](=[O:19])(=[O:18])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[C:14]([F:17])([F:16])[F:15].[OH-].[Na+].Cl>O1CCOCC1>[F:13][C:10]1[CH:11]=[CH:12][C:7]([NH:6][S:5]([CH2:4][C:3]([OH:20])=[O:2])(=[O:19])=[O:18])=[C:8]([C:14]([F:17])([F:15])[F:16])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 150576042-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]-acetic acid methyl ester

Product 1

HCID 156765552-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.2 g (6.98 mmol) of 2-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]acetic acid methyl ester is dissolved in 20 ml of dioxane, and the solution is combined with 10 ml (20 mmol) of 2N sodium hydroxide solution. The mixture heats up slightly, and saponification is completed after 10 minutes. The solution is neutralized with 2N hydrochloric acid under pH control and gently evaporated to dryness under vacuum. The residue is extracted with 30 ml of ethyl acetate, the solution is extracted once by shaking with 10 ml of water, the organic phase is dried over magnesium sulfate, filtered, and evaporated to dryness, thus obtaining 1.96 g (6.51 mmol)=93.2% of theory.

Workup

  1. customgently evaporated to dryness under vacuum
  2. extractionThe residue is extracted with 30 ml of ethyl acetate
  3. extractionthe solution is extracted once
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customthus obtaining 1.96 g (6.51 mmol)=93.2% of theory

Sources & evidence

ORD record
ord-cbda5d5848914e98969cbceb8642d5f2
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Linked notes

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