Ethyl benzoate → HCID 13649194, compound

HRID 648983Notes

Reaction equation

HRID 648983 reaction equation
[C:1](OCC)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[O-].[Na+].Cl.[N:17]1([C:23]([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[NH:30][C:29](=[O:34])[CH2:28]3)=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C(O)C>[C:1]([N:20]1[CH2:21][CH2:22][N:17]([C:23]([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[NH:30][C:29](=[O:34])[CH2:28]3)=[O:24])[CH2:18][CH2:19]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7165Ethyl benzoateHCID 2723922Sodium ethoxideHCID 13649192HCID 13649192, compound

Product 1

HCID 13649194HCID 13649194, compoundYield 6.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 100 ml of ethanol were added 1.36 g of ethyl benzoate, 0.5 g of sodium ethylate and 2.6 g of 5-(piperazinylcarbonyl)oxindol hydrochloride and the mixture was reacted in an autocrave at 140° to 150° C. under 110 atm for 6 hours. After cooling, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in 200 ml of chloroform. After washing, in turn, with 1% aqueous potassium carbonate solution, dilute hydrochloric acid, and water, the chloroform solution was dried over anhydrous sodium sulfate and the solvent was distilled off. The resultant residue was purified by silica-gel column chromatography [silica-gel: WAKO C-200, eluent: chloroform:methanol (V/V)=20:1], and the crude crystal was recrystallized from methanol to give 215 mg of 5-(4-benzoyl-1-piperazinylcarbonyl)oxindol.

Workup

  1. customthe mixture was reacted in an autocrave at 140° to 150° C. under 110 atm for 6 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 200 ml of chloroform
  5. washAfter washing, in turn, with 1% aqueous potassium carbonate solution, dilute hydrochloric acid, and water
  6. dry with materialthe chloroform solution was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe resultant residue was purified by silica-gel column chromatography [silica-gel: WAKO C-200, eluent: chloroform:methanol (V/V)=20:1]
  9. customthe crude crystal was recrystallized from methanol

Sources & evidence

ORD record
ord-561ac4c04bcb4b0f98c4ec0d27aa3a5d
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

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