Ethanol → HCID 9846356, compound

HRID 1938342Notes

Reaction equation

HRID 1938342 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[C:20]([CH2:25][CH:26]3[S:30][C:29](=N)[NH:28][C:27]3=[O:32])[CH:21]=[N:22]2)=[CH:17][CH:16]=1.C([OH:35])C>Cl>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[C:20]([CH2:25][CH:26]3[S:30][C:29](=[O:35])[NH:28][C:27]3=[O:32])[CH:21]=[N:22]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 140385021HCID 140385021, compound

Product 1

HCID 9846356HCID 9846356, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In a mixture of 3N hydrochloric acid (4 mL) and ethanol (2 mL) was dissolved 5-[[7-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-quinolyl]methyl]-2-iminothiazolidin-4-one (100 mg, 0.22 mmol.). The resulting solution was heated under reflux for 12 hours. After the completion of reaction was confirmed, ethanol was distilled off. To the residue were added ethyl acetate and aqueous sodium hydrogen carbonate. The organic portion was recovered, washed with water, and dried over sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3), to give 11 mg of the desired compound as pale brown crystalline powder (yield 11%).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 12 hours
  3. customAfter the completion of reaction
  4. distillationethanol was distilled off
  5. additionTo the residue were added ethyl acetate and aqueous sodium hydrogen carbonate
  6. customThe organic portion was recovered
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3)

Sources & evidence

ORD record
ord-0ad267cc8b2c4946926d83cb1dd63dda
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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