Potassium Carbonate → 4-(Phenylsulfamoyl)phenyl 4-ethenylbenzoate

HRID 1633163Notes

Reaction equation

HRID 1633163 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:28]=[CH:27][C:7]([C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17](=[O:26])(=[O:25])[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:3]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17](=[O:25])(=[O:26])[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=1)=[CH2:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 204418094-(Phenylsulfamoyl)phenyl 4-(2-bromoethyl)benzoate

Product 1

HCID 204418184-(Phenylsulfamoyl)phenyl 4-ethenylbenzoateYield 76.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 18.5 g (0.0402 mol) of 4-(N-phenylsulfamoyl)phenyl 4-(2-bromoethyl)benzoate, 5.55 g (0.0402 mol) of potassium carbonate and 250 ml of acetone was stirred at room temperature for approximately 48 hours. The mixture was filtered and concentrated to an oily solid. Recrystallization from ethanol:water gave 11.7 g (76.7% of theory) of 4-(N-phenylsulfamoyl)phenyl 4-vinylbenzoate; mp=59°-60° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated to an oily solid
  3. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-d8a37e776cf24f558a0f0ecd6e81495c
Source dataset
uspto-grants-1984_10
Patent number
US04478992

Reaction notes

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