Benzaldehyde → HCID 2851580, compound

HRID 1721549Notes

Reaction equation

HRID 1721549 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:10]1([N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>O1CCCC1>[C:10]1([N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=[CH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 962WaterHCID 10738Hydrazine, 1,1-diphenyl-, hydrochloride (1:1)

Product 1

HCID 2851580HCID 2851580, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 500 parts of tetrahydrofuran were dissolved 23.8 parts of 4- 5-(5H-dibenzo b,f!azepinyl)!benzaldehyde and 26.5 parts of N,N-diphenylhydrazine hydrochloride. This solution was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into 2,000 parts of water, and the crystals precipitated were taken out by filtration. The crystals obtained were washed with ethyl alcohol and then dried at reduced pressure. The crystals dried were dissolved in 100 parts of ethyl acetate, and this solution was poured into 1,000 parts of methyl alcohol to recrystallize the reaction product. Thus, 28.9 parts (yield, 77.9%) of 4- 5-(5H-dibenzo b,f!azepinyl)!benzaldehyde N,N-diphenylhydrazone was obtained. This compound had a melting point of 178.0° to 179.0° C. The results of elemental analysis are shown in Table 4 below, together with calculated values for C33H25N3.

Workup

  1. customAfter completion of the reaction
  2. customthe crystals precipitated
  3. filtrationwere taken out by filtration
  4. customThe crystals obtained
  5. washwere washed with ethyl alcohol
  6. customdried at reduced pressure
  7. customThe crystals dried
  8. dissolutionwere dissolved in 100 parts of ethyl acetate
  9. additionthis solution was poured into 1,000 parts of methyl alcohol
  10. customto recrystallize the reaction product
  11. customThus, 28.9 parts (yield, 77.9%) of 4- 5-(5H-dibenzo b,f

Sources & evidence

ORD record
ord-cfab5c85a06d47b5bcc35dda12acf548
Source dataset
uspto-grants-1996_04
Patent number
US05512400

Reaction notes

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