Potassium Carbonate → HCID 18544095, compound

HRID 1268102Notes

Reaction equation

HRID 1268102 reaction equation
C(O[C:9]1[CH:27]=[CH:26][CH:25]=[CH:24][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20](=[O:23])(=[O:22])[NH2:21])=[O:12])C1C=CC=CC=1.[F:28][C:29]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32].[C:39](=[O:42])([O-])[O-].[K+].[K+]>O.O1CCOCC1>[CH2:39]([O:42][C:25]1[CH:24]=[C:10]([CH:9]=[CH:27][CH:26]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([NH:21][C:31](=[O:32])[C:30]1[CH:34]=[CH:35][C:36]([F:38])=[CH:37][C:29]=1[F:28])(=[O:22])=[O:23])=[O:12])[C:9]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5880812,4-Difluorobenzoyl chlorideHCID 18544083HCID 18544083, compound

Product 1

HCID 18544095HCID 18544095, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A 300 mg (0.78 mmol) portion of benzyloxy-N-(2-sulfamoylphenyl)benzamide, 273 mg (1.55 mmol) of 2,4-difluorobenzoyl chloride and 374 mg (2.70 mmol) of potassium carbonate were dissolved in a mixed solvent (10 ml) of water and dioxane (1:1) and stirred at room temperature for 18 hours. After completion of the reaction, the solvent was evaporated under a reduced pressure. The resulting residue was extracted with ethyl acetate, washed with water and saturated brine in that order and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography to obtain 350 mg (yield: 86.0%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under a reduced pressure
  3. extractionThe resulting residue was extracted with ethyl acetate
  4. washwashed with water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-a827dacb66d648a4b9ee207fc61603d6
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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