Methyl iodide → HCID 131721177, compound

HRID 1418310Notes

Reaction equation

HRID 1418310 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].CI.[C:23](=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][CH3:23])=[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 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 131721175HCID 131721175, compound

Product 1

HCID 131721177HCID 131721177, compoundYield 132.5%

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 (0.62 g, 2.0 mmol), methyliodide (0.25 mL, 4 mmol) and potassium carbonate (0.21 g, 1.5 mmol) was stirred for 2 hours under reflux. A saturated ammonium chloride solution (20 mL) was added to the resulting mixture and the organic layer was separated. The aqueous layer was extracted with diethyl ether (10 mL×2 times), 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 crystallization from dichloromethane to obtain a white solid of 2-(2,4-dichloro-5-methyloxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.65 g, yield:100%).

Workup

  1. temperatureunder reflux
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with diethyl ether (10 mL×2 times)
  4. washthe organic layer combined was washed with a saturated sodium chloride solution (40 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of magnesium sulfate
  7. filtrationby filtration
  8. customthe filtrate was evaporated
  9. customto give crude product, which
  10. customwas purified by crystallization from dichloromethane

Sources & evidence

ORD record
ord-f4f85272e18f49f8bf35d0447deb9b56
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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