Benzaldehyde → 1-Benzylidene-2-{4-[4-(4-chlorobenzoyl)benzyl]-3,5-dichlorophenyl}hydrazine

HRID 1602882Notes

Reaction equation

HRID 1602882 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([C:8]2[CH:23]=[CH:22][C:11]([CH2:12][C:13]3[C:19]([Cl:20])=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=3[Cl:21])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[N:26]([O-])=O.[Na+].[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O.O.Cl[Sn]Cl>C(O)(=O)C.O.Cl>[CH:30](=[N:26][NH:17][C:16]1[CH:18]=[C:19]([Cl:20])[C:13]([CH2:12][C:11]2[CH:22]=[CH:23][C:8]([C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:25][CH:24]=3)=[CH:9][CH:10]=2)=[C:14]([Cl:21])[CH:15]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 61436Stannous chloride dihydrateHCID 196083004-[4-(4-Chlorobenzoyl)benzyl]-3,5-dichloroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 701060661-Benzylidene-2-{4-[4-(4-chlorobenzoyl)benzyl]-3,5-dichlorophenyl}hydrazineYield 40%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

In 15 ml of acetic acid was dissolved 2.10 g of 4-[4-(4-chlorobenzoyl)benzyl]-3,5-dichloroaniline, and 1.8 ml of conc. hydrochloric acid was added. A solution of 0.41 g of NaNO2 in 1 ml of water was dropwise added to the mixture with stirring at 5 to 10 uA for a period of 10 minutes. The pale brown mixture was stirred at the same temperature for 1 hour, and then 0.60 g of benzaldehyde was added. A solution of 3.36 g of SnCl2.2H2O in 3.4 ml of conc. hydrochloric acid was added for a period of 15 minutes, and the resulting mixture was reacted at 20 to 25° C. for 3 hours. Precipitated crystals were collected by filtration and recrystallized from ethyl acetate to give the above-identified compound as yellow cryatals (yield: 40%).

Workup

  1. additionwas added
  2. stirringThe pale brown mixture was stirred at the same temperature for 1 hour
  3. customthe resulting mixture was reacted at 20 to 25° C. for 3 hours
  4. customPrecipitated crystals
  5. filtrationwere collected by filtration
  6. customrecrystallized from ethyl acetate
  7. customto give the above-identified compound as yellow cryatals (yield: 40%)

Sources & evidence

ORD record
ord-3574be1de79748c6a1b802b666961852
Source dataset
uspto-grants-1999_11
Patent number
US05985875

Reaction notes

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