3-Methyl-2-butenoyl chloride → 3-Methyl-N-[2-(4-phenylethynylbenzamido)benzenesulfonyl]-2-butenamide

HRID 1268136Notes

Reaction equation

HRID 1268136 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4](Cl)=[O:5].[C:8]1([C:14]#[C:15][C:16]2[CH:34]=[CH:33][C:19]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29](=[O:32])(=[O:31])[NH2:30])=[O:21])=[CH:18][CH:17]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([NH:30][S:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[NH:22][C:20](=[O:21])[C:19]1[CH:33]=[CH:34][C:16]([C:15]#[C:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:17][CH:18]=1)(=[O:31])=[O:32])=[O:5]

Participants

5

Reactant 2

HCID 1023943-Methyl-2-butenoyl chlorideHCID 120430434-Phenylethynyl-N-(2-sulfamoylphenyl)benzamide

Product 1

HCID 590574153-Methyl-N-[2-(4-phenylethynylbenzamido)benzenesulfonyl]-2-butenamideYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and at 0° C., 0.10 ml (0.96 mmol) of 3,3-dimethylacryloyl chloride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 300 mg (0.80 mmol) of 4-phenylethynyl-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 10 and 195 mg (1.60 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 183 mg (yield: 50.0%) 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-c74f775a76e945b6b923c1d47c6884fa
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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