Hexanoyl chloride → N-[2-(4-Phenylethynylbenzamido)benzenesulfonyl]acetamide

HRID 1268133Notes

Reaction equation

HRID 1268133 reaction equation
[C:1](Cl)(=[O:7])[CH2:2]CCCC.[C:9]1([C:15]#[C:16][C:17]2[CH:35]=[CH:34][C:20]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:30](=[O:33])(=[O:32])[NH2:31])=[O:22])=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C)C1C=CN=CC=1.O1CCCC1>[C:9]1([C:15]#[C:16][C:17]2[CH:35]=[CH:34][C:20]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:30]([NH:31][C:1](=[O:7])[CH3:2])(=[O:33])=[O:32])=[O:22])=[CH:19][CH:18]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 67340Hexanoyl chlorideHCID 120430434-Phenylethynyl-N-(2-sulfamoylphenyl)benzamide

Product 1

HCID 59057402N-[2-(4-Phenylethynylbenzamido)benzenesulfonyl]acetamideYield 84.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and at 0° C., 0.20 ml (1.46 mmol) of hexanoyl chloride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 500 mg (1.30 mmol) of 4-phenylethynyl-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 10 and 320 mg (2.60 mmol) of 4-dimethylaminopyridine, the mixture was stirred at room temperature for 1 hour and then the solvent was evaporated under a reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with water, a potassium hydrgensulfate aqueous solution 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 460 mg (yield: 74.6%) of the title compound.

Workup

  1. customthe solvent was evaporated under a reduced pressure
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materiala potassium hydrgensulfate aqueous solution and saturated brine in that order and dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-f3845f1e71d94c06b0b1a1aa6dcde4b9
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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