Benzaldehyde → HCID 14100160, compound

HRID 2232268Notes

Reaction equation

HRID 2232268 reaction equation
[C:1]1([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:11][CH2:10][CH2:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[K+].CCCCCC>CO.C(OCC)(=O)C>[C:1]1([C:7]2[C:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[N:11][C:10]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 8058HexaneHCID 14797Potassium HydroxideHCID 2562185,6-diphenyl-2,3-dihydropyrazine

Product 1

HCID 14100160HCID 14100160, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 20 ml of methanol were dissolved 2.570 g of 2,3-diphenyl-5,6-dihydropyrazine, 1.060 g of benzaldehyde and 0.672 g of potassium hydroxide. The solution was heated under reflux for 1 hour. Methanol was removed from the reaction solution by distillation under reduced pressure, and to the residue was added 50 ml of water. The resulting mixture was extracted three times with ethyl acetate. The organic layer from the extraction was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was subjected to column chromatography on silica gel. A crude product was obtained from the eluates with an 8:1 hexane : ethyl acetate mixture. The crude product was recrystallized from hexane to give 2.940 g of 2,3-diphenyl-5-benzylpyrazine as colorless prisms. M.P. 118°-119° C. Physical properties of the product support a chemical structure of the below formula (VII).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 1 hour
  3. customMethanol was removed from the reaction solution by distillation under reduced pressure
  4. additionto the residue was added 50 ml of water
  5. extractionThe resulting mixture was extracted three times with ethyl acetate
  6. extractionThe organic layer from the extraction
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe residue thus obtained
  11. customThe crude product was recrystallized from hexane

Sources & evidence

ORD record
ord-fe1d727fecfc4d09a94574323bfac3e5
Source dataset
uspto-grants-1988_11
Patent number
US04788197

Reaction notes

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