Propargyl bromide → HCID 131721179, compound

HRID 1418312Notes

Reaction equation

HRID 1418312 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:18](=[O:19])[C:13]2=[CH:14][CH2:15][CH2:16][CH2:17][N:12]2[C:11]1=[O:20].[CH2:21](Br)[C:22]#[CH:23].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:23][C:22]#[CH:21])=[CH:4][C:3]=1[N:10]1[C:18](=[O:19])[C:13]2=[CH:14][CH2:15][CH2:16][CH2:17][N:12]2[C:11]1=[O:20]

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 131721175HCID 131721175, compound

Product 1

HCID 131721179HCID 131721179, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An acetonitrile (10 mL) solution of 2-(2,4-dichloro-5-hydroxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.50 g, 1.61 mmol), propargylbromide (0.16 mL, 1.77 mmol) and potassium carbonate (0.22 g, 1.61 mmol) was stirred for 3 hours under reflux. A saturated ammonium chloride solution (20 mL) was added to the resulting mixture and the organic layer combined was washed with a saturated sodium chloride solution (40 mL) and dried over anhydrous magnesium sulfate. After removal of magnesium sulfate by filtration, the filtrate was evaporated to give crude product, which was purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/2) to obtain a white solid of 2-(2,4-dichloro-5-propargyloxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.41 g, yield:73.2%).

Workup

  1. temperatureunder reflux
  2. washthe organic layer combined was washed with a saturated sodium chloride solution (40 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removal of magnesium sulfate
  5. filtrationby filtration
  6. customthe filtrate was evaporated
  7. customto give crude product, which
  8. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-8310bb03dfa34c02b622907b0e4bdc89
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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