4-Toluenesulfonyl chloride → trans-N-[2-(4-Phenylethynylbenzamido)benzenesulfonyl]-3-hexenamide

HRID 1268138Notes

Reaction equation

HRID 1268138 reaction equation
S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[C:12]([OH:19])(=O)[CH2:13][CH:14]=[CH:15][CH2:16][CH3:17].[C:20]1([C:26]#[C:27][C:28]2[CH:46]=[CH:45][C:31]([C:32]([NH:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[S:41](=[O:44])(=[O:43])[NH2:42])=[O:33])=[CH:30][CH:29]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C1C=CN=CC=1.O1CCCC1>[C:20]1([C:26]#[C:27][C:28]2[CH:46]=[CH:45][C:31]([C:32]([NH:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[S:41]([NH:42][C:12](=[O:19])[CH2:13]/[CH:14]=[CH:15]/[CH2:16][CH3:17])(=[O:43])=[O:44])=[O:33])=[CH:30][CH:29]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 20200Hex-3-enoic acidHCID 120430434-Phenylethynyl-N-(2-sulfamoylphenyl)benzamide

Product 1

HCID 12972896trans-N-[2-(4-Phenylethynylbenzamido)benzenesulfonyl]-3-hexenamideYield 66.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and at 0° C., 249 mg (1.30 mmol) of tosylic chloride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 149 mg (1.30 mmol) of 3-hexenoic acid and 532 mg (4.35 mmol ) of 4-dimethylaminopyridine, and the mixture was stirred for 1 hour. Next, this was mixed with 300 mg (0.80 mmol) of 4-phenylethynyl-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 10 and 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 chromatography to obtain 250 mg (yield: 65.0%) of the title compound.

Workup

  1. customproduced in Reference Example 10
  2. stirringstirred at room temperature for 1 hour
  3. customthe solvent was evaporated under a reduced pressure
  4. dissolutionThe resulting residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materiala potassium hydrgensulfate aqueous solution and saturated brine in that order and dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under a reduced pressure
  8. customThe resulting residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-df07894efb39400a8b8f6acc4265ed22
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

Loading…