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Sodium Hydroxide → 5-Methylsulfamoyl-2-(2,2,2-trifluoro-ethoxy)-benzoic acid

HRID 2251244
Notes
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Reaction equation

HRID 2251244 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([S:10](=[O:14])(=[O:13])[NH:11][CH3:12])[CH:7]=[CH:6][C:5]=1[O:15][CH2:16][C:17]([F:20])([F:19])[F:18].[OH-].[Na+]>C1COCC1>[CH3:12][NH:11][S:10]([C:8]1[CH:7]=[CH:6][C:5]([O:15][CH2:16][C:17]([F:19])([F:18])[F:20])=[C:4]([CH:9]=1)[C:3]([OH:21])=[O:2])(=[O:13])=[O:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 577537255-Methylsulfamoyl-2-(2,2,2-trifluoro-ethoxy)-benzoic acid methyl ester

Product 1

HCID 577535975-Methylsulfamoyl-2-(2,2,2-trifluoro-ethoxy)-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 2.3 mmol 5-methylsulfamoyl-2-(2,2,2-trifluoro-ethoxy)-benzoic acid methyl ester in 10 ml THF was added 20 mmol 2 M aq NaOH, and the mixture was heated at 50° C. for 2 h. The mixture was then cooled to RT and extracted twice with ether. The aqueous phase was acidified with 10% aq citric acid and extracted 3 times with ethyl acetate. The combined organic phases were dried with Na2SO4. Evaporation in vacuo followed by trituration in ether afforded the tide compound. MS (m/e): 312.0 ([M−H]−, 100%)

Workup

  1. temperatureThe mixture was then cooled to RT
  2. extractionextracted twice with ether
  3. extractionextracted 3 times with ethyl acetate
  4. dry with materialThe combined organic phases were dried with Na2SO4
  5. customEvaporation in vacuo
  6. customafforded the tide compound

Sources & evidence

ORD record
ord-25cdf557b3fe410eb691b06a266b90ab
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07319099B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes