Propargyl bromide → HCID 20089150, compound

HRID 274862Notes

Reaction equation

HRID 274862 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([CH2:13][CH3:14])[C:11](=[O:15])[N:10]=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]#[CH:24]>CC(C)=O>[CH2:24]([N:10]1[C:11](=[O:15])[N:12]([CH2:13][CH3:14])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:9]1)[C:23]#[CH:22]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 67790043HCID 67790043, compound

Product 1

HCID 20089150HCID 20089150, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the solution of 3-(4-chlorophenyl)-4-ethyl-1,2,4-triazolin-5-one (2.23 g, 0.01 mole) in dry acetone (40 ml) was added, at room temperature, potassium carbonate (1.67 g, 0.012 mole) followed by propargyl bromide (1.8 g of 80% in toluene, 0.012 mole). The reaction mixture was then refluxed with stirring for 6 hr. The mixture was cooled down to room temperature and solvent was evaporated to give a residue. The product was purified by crystallization from hexane/ether, affording 1.8 g (69.2% yield) of 1-propargyl-3-(4-chlorophenyl)-4-ethyl-1,2,4-triazolin-5-one as a white solid. m.p.=115°-119° C. A proton NMR spectrum was consistent with the desired structure.

Workup

  1. temperatureThe reaction mixture was then refluxed
  2. customsolvent was evaporated
  3. customto give a residue
  4. customThe product was purified by crystallization from hexane/ether

Sources & evidence

ORD record
ord-531e31bbeff14957ab689737d77b0b2d
Source dataset
uspto-grants-1995_02
Patent number
US05391561

Reaction notes

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