Hydrochloric Acid → HCID 131721184, compound

HRID 1418316Notes

Reaction equation

HRID 1418316 reaction equation
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:4][SH:5].[F:10][C:11]1[CH:16]=[C:15](F)[C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]=1[N:21]1[C:29](=[O:30])[C:24]2=[CH:25][CH2:26][CH2:27][CH2:28][N:23]2[C:22]1=[O:31].Cl>C(OCC)(=O)C.O1CCOCC1>[CH2:8]([O:7][C:3]([CH2:4][S:5][C:15]1[C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]([N:21]2[C:29](=[O:30])[C:24]3=[CH:25][CH2:26][CH2:27][CH2:28][N:23]3[C:22]2=[O:31])=[C:11]([F:10])[CH:16]=1)=[O:6])[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 131721183HCID 131721183, compound

Product 1

HCID 131721184HCID 131721184, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium hydride (1.20 g, 0.03 mol) was put in to a flask, to which 1,4-dioxane (100 mL) and ethyl thioglycolate (1.83 mL, 0.017 mol) was added with stirring under cooling in an ice-water bath after replacing the inside of flask throughly with argon gas, and the mixture was stirred for 15 minutes at the ambient temperature. Then, 2-(2,4-difluoro-5-nitrophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (4.7 g, 0.015 mol) was added to the mixture at the same temperature. The reaction mixture was wormed up to room temperature and stirred for 24 hours. 1N Hydrochloric acid (100 mL) and ethyl acetate (100 mL) were added to the resulting mixture and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (50 mL×2 times). The organic layer combined was washed with a saturated sodium bicarbonate (100 mL) and a saturated sodium chloride solution (100 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=1/1) to obtain a white solid of 2-(4-ethoxycarbonylmethylthio-2-fluoro-5-nitrophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (1.83 g, yield:29.8%).

Workup

  1. additionwas added
  2. temperatureunder cooling in an ice-water bath
  3. stirringthe mixture was stirred for 15 minutes at the ambient temperature
  4. customwas wormed up to room temperature
  5. stirringstirred for 24 hours
  6. customthe organic layer was separated
  7. extractionThe aqueous layer was extracted with ethyl acetate (50 mL×2 times)
  8. washThe organic layer combined was washed with a saturated sodium bicarbonate (100 mL)
  9. dry with materiala saturated sodium chloride solution (100 mL), and dried over anhydrous magnesium sulfate
  10. customAfter removal of magnesium sulfate
  11. filtrationby filtration
  12. customthe filtrate was evaporated
  13. customto give crude product, which
  14. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-1df6a46b28f54c8fa3209cca50f5d11b
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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