3-Phenylprop-2-enoyl chloride → N-[2-[3-(4-t-Butylbenzyloxy)benzamido]benzenesulfonyl]cinnamamide

HRID 1268105Notes

Reaction equation

HRID 1268105 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]([C:16]1[CH:42]=[CH:41][C:19]([CH2:20][O:21][C:22]2[CH:23]=[C:24]([CH:38]=[CH:39][CH:40]=2)[C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34](=[O:37])(=[O:36])[NH2:35])=[O:26])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]>CN(C)C1C=CN=CC=1.O1CCCC1>[C:12]([C:16]1[CH:42]=[CH:41][C:19]([CH2:20][O:21][C:22]2[CH:23]=[C:24]([CH:38]=[CH:39][CH:40]=2)[C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34]([NH:35][C:1](=[O:10])[CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)(=[O:36])=[O:37])=[O:26])=[CH:18][CH:17]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 660233-Phenylprop-2-enoyl chlorideHCID 120413093-(4-t-Butylbenzyloxy)-N-(2-sulfamoylphenyl)benzamide

Product 1

HCID 69970292N-[2-[3-(4-t-Butylbenzyloxy)benzamido]benzenesulfonyl]cinnamamideYield 95.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and at 0° C., 126 mg (0.75 mmol) of cinnamoyl chloride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 300 mg (0.68 mmol) of 3-(4-t-butylbenzyloxy)-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 2 and 167 mg (1.36 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 crude crystals were washed with methanol to obtain 370 mg (yield: 95.0%) 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. washThe resulting crude crystals were washed with methanol

Sources & evidence

ORD record
ord-e77532cee8894f9485b9934643c3321b
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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