Sodium Hydroxide → HCID 69036733, compound

HRID 1820786Notes

Reaction equation

HRID 1820786 reaction equation
C[O:2][C:3](=[O:20])[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][CH:17]([CH3:19])[CH3:18].[OH-].[Na+]>C1COCC1>[CH2:16]([O:15][C:5]1[CH:6]=[CH:7][C:8]([S:10](=[O:14])(=[O:13])[NH:11][CH3:12])=[CH:9][C:4]=1[C:3]([OH:20])=[O:2])[CH:17]([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69037483HCID 69037483, compound

Product 1

HCID 69036733HCID 69036733, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 3.3 mmol 2-isobutoxy-5-methylsulfamoyl-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): 286.2 ([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

Sources & evidence

ORD record
ord-ac60dc8835a84f7bbd216969f552467c
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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