Methyl chloroacetate → HCID 131721168, compound

HRID 1418303Notes

Reaction equation

HRID 1418303 reaction equation
[Cl:1][C:2]1C(O)=[CH:6][C:5]([N:9]2[C:17](=[O:18])[C:12]3=[CH:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1.[C:21](=[O:24])([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]([O:31][CH3:32])=[O:30].[Cl-].[NH4+]>C(#N)C>[Cl:1][C:2]1[C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:6][C:5]([N:9]2[C:17](=[O:18])[C:12]3=[CH:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[O:19])=[C:4]([F:20])[C:3]=1[O:24][CH3:21]

Participants

6

Reactant 4

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 15390589HCID 15390589, compound

Product 1

HCID 131721168HCID 131721168, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An acetonitrile (10 mL) solution of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.59 g, 2.0 mmol), potassium carbonate (0.2 g, 2.2 mmol) and methyl chloroacetate (0.2 mL, 2.2 mmol) was stirred for 5 hours under reflux. A saturated ammonium chloride solution (10 mL) was added to the resulting mixture, and the organic layer was separated and then the aqueous layer was extracted with diethyl ether (10 mL×2 times). The organic layer combined was washed with a saturated sodium chloride solution (20 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 2-(4-chloro-2-fluoro-5-methoxycarbonyl-methoxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.64 g, yield:86.5%).

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 (20 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 silica gel column (Wakogel C-200, ethyl acetate/hexane =1/2)

Sources & evidence

ORD record
ord-b1a9bb0163f6408f8e8c5432189a6f8b
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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