Propargyl bromide → HCID 19863042, compound

HRID 1164716Notes

Reaction equation

HRID 1164716 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH2:15][CH2:16][CH2:17][F:18])[C:11]([CH3:19])=[N:10]2)=[C:4]([F:20])[CH:3]=1.[CH2:21](Br)[C:22]#[CH:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[C:7]([O:8][CH2:23][C:22]#[CH:21])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH2:15][CH2:16][CH2:17][F:18])[C:11]([CH3:19])=[N:10]2)=[C:4]([F:20])[CH:3]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 19863044HCID 19863044, compound

Product 1

HCID 19863042HCID 19863042, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 0.5 g (0.002 mole) of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-(3-fluoropropyl)-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one, 0.43 g (0.004 mole) of propargyl bromide and 0.33 g (0.002 mole) of potassium carbonate in 20 mL of acetone was heated under reflux for 5 hours. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The residual oil was subjected to column chromatography on silica gel using 4:1 methylene chloride:heptane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure to give 0.42 g of 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4-(3-fluoropropyl)-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one as an oil.

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e31e265fc5584b3f910b02696daf6e93
Source dataset
uspto-grants-1990_03
Patent number
US04906284

Reaction notes

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