Allyl bromide → 2-[(Prop-2-en-1-yl)oxy]benzene-1-sulfonamide

HRID 2295467Notes

Reaction equation

HRID 2295467 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>C(C(C)=O)C>[CH2:20]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:9])=[O:10])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 6375462-Hydroxybenzene-1-sulfonamide

Product 1

HCID 133217572-[(Prop-2-en-1-yl)oxy]benzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3.5 g of 2-hydroxyphenylsulfonamide, 5.5 g of potassium carbonate and 1.7 ml of allyl bromide in 100 ml of methyl ethyl ketone is stirred, under nitrogen, for 1 hour at reflux temperature. The reaction mixture is cooled to room temperature, filtered, and evaporated to dryness. Once recrystallisation from ethyl acetate yields 3.27 g of 2-allyloxyphenylsulfonamide with a melting point of 104°-105° C.

Workup

  1. temperatureat reflux temperature
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customOnce recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-912676ed164848e4abeba5091e09c725
Source dataset
uspto-grants-1984_01
Patent number
US04425154

Reaction notes

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