Propargyl bromide → 5-Methyl-2-propargyloxyphenylsulfonamide

HRID 325800Notes

Reaction equation

HRID 325800 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]#[CH:21]>C(#N)C>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:21][C:20]#[CH:19])=[C:3]([S:9]([NH2:12])(=[O:10])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 133217532-Hydroxy-5-methylbenzenesulfonamide

Product 1

HCID 134729485-Methyl-2-propargyloxyphenylsulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 24.3 g of 2-hydroxy-5-methylphenylsulfonamide, 36.0 g of potassium carbonate, 16.7 g of propargyl bromide and 500 ml of acetonitrile is stirred at 50° C. for 4.5 hours. The reaction mixture is then filtered, and concentrated by evaporation. The yield after recrystallisation from ethyl acetate is 23.9 g of 5-methyl-2-propargyloxyphenylsulfonamide, m.p. 169°-170° C.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated by evaporation
  3. customThe yield
  4. customafter recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-d53deda4f1d5454b91096332035a5f37
Source dataset
uspto-grants-1984_04
Patent number
US04443243

Reaction notes

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