Thionyl Chloride → 4-Phenylethynyl-N-(2-sulfamoylphenyl)benzamide

HRID 1268131Notes

Reaction equation

HRID 1268131 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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]>C1C=CC=CC=1>[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29](=[O:31])(=[O:30])[NH2:32])=[O:15])=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 728942-AminobenzenesulfonamideHCID 43089034-(2-Phenylethynyl)benzoic acid

Product 1

HCID 120430434-Phenylethynyl-N-(2-sulfamoylphenyl)benzamideYield 78.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A benzene (30 ml) solution containing 3.00 g (13.5 mmol) of 4-phenylethynylbenzoic acid and 2 ml of thionyl chloride was heated under reflux for 2 hours and then the solvent was evaporated under a reduced pressure. The resulting residue was dissolved in methylene chloride (30 ml), this solution was added dropwise under ice-cooling to a pyridine (50 ml) solution containing 2.32 g (13.50 mmol) of 2-aminobenzenesulfonamide, the mixture was stirred at room temperature for 18 hours and then methylene chloride was evaporated under a reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with a 1 N hydrochloric acid aqueous solution, 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 recrystallized from ethyl acetate-hexane to obtain 4.00 g (yield: 78.7%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customthe solvent was evaporated under a reduced pressure
  4. dissolutionThe resulting residue was dissolved in methylene chloride (30 ml)
  5. additionthis solution was added dropwise under ice-
  6. temperaturecooling to a pyridine (50 ml) solution
  7. custommethylene chloride was evaporated under a reduced pressure
  8. dissolutionThe resulting residue was dissolved in ethyl acetate
  9. washwashed with a 1 N hydrochloric acid aqueous solution, water and saturated brine in that order
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was evaporated under a reduced pressure
  12. customThe resulting residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-205b1f2b980f44a08d01773032056356
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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