Potassium Carbonate → 5-Methylsulfamoyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid methyl ester

HRID 225714Notes

Reaction equation

HRID 225714 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([S:10](=[O:14])(=[O:13])[NH:11][CH3:12])[CH:7]=[CH:6][C:5]=1[OH:15].C(=O)([O-])[O-].[K+].[K+].[F:23][C:24]([F:36])([F:35])[CH:25](OS(C(F)(F)F)(=O)=O)[CH3:26]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:16])[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][CH:25]([CH3:26])[C:24]([F:36])([F:35])[F:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 230467632-Hydroxy-5-methylsulfamoyl-benzoic acid methyl esterHCID 574452801, 1, 1-Trifluoropropan-2-yl trifluoromethanesulfonatc

Product 1

HCID 577534755-Methylsulfamoyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 4.1 mmol 2-hydroxy-5-methylsulfamoyl-benzoic acid methyl ester and 4.1 mmol potassium carbonate in 5 ml DMF was added dropwise 6.1 mmol trifluoro-methanesulfonic acid 2,2,2-trifluoro-1-methyl-ethyl ester and the mixture was heated at 90° C. for 16 h. The mixture was then cooled to RT, poured onto water and extracted 3 times with ethyl acetate. The combined organic phases were dried with Na2SO4. Evaporation in vacuo followed by chromatography on silica gel (eluant: dichloromethane) afforded the title compound. MS (m/e): 359.2 (M+NH4+, 80%), 342.0 (M+H+, 100%)

Workup

  1. temperatureThe mixture was then cooled to RT
  2. additionpoured onto water
  3. extractionextracted 3 times with ethyl acetate
  4. dry with materialThe combined organic phases were dried with Na2SO4
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-5695f2c9b7064476b90ffd82df438fdb
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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