Ethanol → HCID 21469273, compound

HRID 1938338Notes

Reaction equation

HRID 1938338 reaction equation
N=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[C:14]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])[CH:13]=3)[S:3]1.C([OH:33])C>Cl>[F:29][C:27]([F:28])([F:30])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][O:19][C:14]1[CH:13]=[C:12]2[C:17]([CH:18]=[C:9]([CH2:8][CH:4]3[S:3][C:2](=[O:33])[NH:6][C:5]3=[O:7])[CH:10]=[N:11]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 140385019HCID 140385019, compound

Product 1

HCID 21469273HCID 21469273, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In a mixture of 2N hydrochloric acid (5 mL) and ethanol (3 mL) was dissolved 2-imino-5-[[7-(2-trifluoromethylbenzyloxy)-3-quinolyl]methyl]thiazolidin-4-one (200 mg, 0.47 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 so that the aqueous phase was made to pH 7. 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=1/8), to give 89 mg of the desired compound as pale brown crystalline powder (yield 44%).

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 so that the aqueous phase
  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=1/8)

Sources & evidence

ORD record
ord-a79843505b784b3097cada341b81979a
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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