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

HRID 1820788Notes

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]

Participants

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 title compound. MS (m/e): 312.0 ([M−H]−, 100%)

Workup

temperatureThe mixture was then cooled to RT
extractionextracted twice with ether
extractionextracted 3 times with ethyl acetate
dry with materialThe combined organic phases were dried with Na2SO4
customEvaporation in vacuo

Sources & evidence

ORD record: ord-44059217e68745819113e2e252e901e4
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605163B2

Reaction notes

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