Potassium Carbonate → 4-[(Methanesulfonyl)amino]phenyl 4-ethenylbenzoate

HRID 904927Notes

Reaction equation

HRID 904927 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:23]=[CH:22][C:7]([C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[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:23]=[CH:22][C:7]([C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][S:18]([CH3:21])(=[O:19])=[O:20])=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=1)=[CH2:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 204418104-[(Methanesulfonyl)amino]phenyl 4-(2-bromoethyl)benzoate

Product 1

HCID 204418074-[(Methanesulfonyl)amino]phenyl 4-ethenylbenzoateYield 52.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 10.0 g (0.02511 mol) of 4-(methanesulfonamido)phenyl 4-(2-bromoethyl)benzoate, 3.47 g (0.02511 mol) of potassium carbonate and 100 ml of acetone was stirred at room temperature for 48 hours. The resultant mixture was filtered and the filtrate was condensed to a solid. Recrystallization from 1:1 1,2-dichloroethane:hexane gave 4.2 g (52.7% of theory) of 4-(methanesulfonamido)phenyl 4-vinylbenzoate; mp=172°-3° C.

Workup

  1. filtrationThe resultant mixture was filtered
  2. customcondensed to a solid
  3. customRecrystallization from 1:1 1,2-dichloroethane

Sources & evidence

ORD record
ord-4c5978d98a1c4639a272dc5833fca68b
Source dataset
uspto-grants-1983_12
Patent number
US04420630

Reaction notes

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