Propargyl bromide → 2-(Prop-2-yn-1-yloxy)benzene-1-sulfonamide

HRID 1248370Notes

Reaction equation

HRID 1248370 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)[C:19]#[CH:20]>CC(CC)=O>[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])[C:19]#[CH:18]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 6375462-Hydroxybenzene-1-sulfonamide

Product 1

HCID 134729452-(Prop-2-yn-1-yloxy)benzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 35 g of 2-hydroxyphenylsulfonamide, 55.2 g of potassium carbonate, 15.5 ml of propargyl bromide and 1000 ml of ethyl methyl ketone is refluxed for 1.5 hours; it is then cooled, filtered, and concentrated by evaporation. The yield after recrystallisation of the residue from ethyl acetate is 30 g of 2-propargyloxyphenylsulfonamide, m.p. 143°-145° C.

Workup

  1. temperatureis refluxed for 1.5 hours
  2. temperatureit is then cooled
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe yield
  6. customafter recrystallisation of the residue from ethyl acetate

Sources & evidence

ORD record
ord-6e9bc27a7cc14df5a6d8cbae85ec2b6d
Source dataset
uspto-grants-1985_06
Patent number
US04523944

Reaction notes

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