Acetic Acid → N-[3,5-Bis(trifluoromethyl)phenyl]-2-methoxy-5-(pyrrole-1-sulfonyl)benzamide

HRID 2384383Notes

Reaction equation

HRID 2384383 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:27])[C:15]2[CH:20]=[C:19]([S:21](=[O:24])(=[O:23])[NH2:22])[CH:18]=[CH:17][C:16]=2[O:25][CH3:26])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CO[CH:32]1[CH2:36][CH2:35][CH:34](OC)O1.C(O)(=O)C>O>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:27])[C:15]2[CH:20]=[C:19]([S:21]([N:22]3[CH:32]=[CH:36][CH:35]=[CH:34]3)(=[O:23])=[O:24])[CH:18]=[CH:17][C:16]=2[O:25][CH3:26])[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 29204801N-[3,5-bis(trifluoromethyl)phenyl]-2-methoxy-5-sulfamoylbenzamide

Product 1

HCID 86595539N-[3,5-Bis(trifluoromethyl)phenyl]-2-methoxy-5-(pyrrole-1-sulfonyl)benzamideYield 88.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-[3,5-bis(trifluoromethyl)phenyl]-2-methoxy-5-sulfamoyl-benzamide (442 mg, 1 mmol), 2,5-dimethoxytetrahydrofuran (159 mg, 1.2 mmol) and acetic acid (5 mL) was refluxed for 2 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water, saturated aqueous sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporating the solvent under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=3:2) to give the title compound (436.5 mg, 88.6%) as a white solid.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washAfter the organic layer was washed with water, saturated aqueous sodium hydrogen carbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe residue obtained
  7. customby evaporating the solvent under reduced pressure
  8. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-a9a8cef450ba430dae7e333b54fb85fe
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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