Potassium Carbonate → HCID 12043041, compound

HRID 1268097Notes

Reaction equation

HRID 1268097 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29]([NH2:32])(=[O:31])=[O:30].[C:33](=[O:36])([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([CH:15]=[CH:11][CH:10]=1)[C:33]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29]([NH:32][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][CH:17]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)(=[O:30])=[O:31])=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 728942-AminobenzenesulfonamideHCID 3092263-(Benzyloxy)benzoic acid

Product 1

HCID 12043041HCID 12043041, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 312751,4-DioxaneSolvent

Procedure

A benzene (10 ml) solution containing 600 mg (2.3 mmol) of 3-benzyloxybenzoic acid and 1.5 ml of thionyl chloride was heated under reflux for 2 hours and then the solvent was evaporated. A dioxane (10 ml) solution of the resulting residue was added dropwise to a water-dioxane 1:1 (10 ml) solution containing 248 mg (1.44 mmol) of 2-amino-benzenesulfonamide and 726 mg (5.2 mmol) of potassium carbonate, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, dioxane was evaporated, the resulting residue was acidified by adding 1 N HCl under ice-cooling and extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. By recrystallizing the resulting residue from acetonitrile, 200 mg (yield: 90%) of the title compound was obtained.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customthe solvent was evaporated
  4. additionA dioxane (10 ml) solution of the resulting residue was added dropwise to a water-dioxane 1:1 (10 ml) solution
  5. customwas evaporated
  6. additionby adding 1 N HCl under ice-
  7. temperaturecooling
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with water and saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was evaporated under a reduced pressure
  12. customBy recrystallizing the resulting residue from acetonitrile

Sources & evidence

ORD record
ord-08822bcd0ebb4415847052e8a166be1a
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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