Hydrochloric Acid → 849419-55-2

HRID 2220150Notes

Reaction equation

HRID 2220150 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]3[S:25][C:24](=N)[NH:23][C:22]3=[O:27])=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].Cl.C([OH:31])C>>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]3[S:25][C:24](=[O:31])[NH:23][C:22]3=[O:27])=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 140513725HCID 140513725, compound

Product 1

HCID 11440398849419-55-2

Procedure

To a suspension of 5-[4-[(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]-2-iminothiazolidin-4-one (6.23 g) in ethanol was added concentrated hydrochloric acid (20 ml) to give a solution, which was stirred under reflux for 24 hrs. After the reaction, the mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate-water, and the solution was neutralized with aqueous sodium bicarbonate. After partitioning and extraction, the extracted organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtrated and concentrated, and the precipitated object compound (5.32 g) was collected by filtration melting point: 221-222° C.

Workup

  1. customto give a solution, which
  2. temperatureunder reflux for 24 hrs
  3. customAfter the reaction
  4. concentrationthe mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate-water
  6. customAfter partitioning
  7. extractionextraction
  8. washthe extracted organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltrated
  11. concentrationconcentrated
  12. filtrationthe precipitated object compound (5.32 g) was collected by filtration melting point: 221-222° C.

Sources & evidence

ORD record
ord-c6c6dcba74a94c389b90ae5ed427eca6
Source dataset
uspto-grants-2008_08
Patent number
US07417052B2

Reaction notes

Loading…