Benzaldehyde → Benzaldehyde 4-(4-chloro-alpha-cyanobenzyl)-3,5-dichlorophenyl hydrazone

HRID 321987Notes

Reaction equation

HRID 321987 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH:6]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([NH:16][NH2:17])=[CH:11][C:10]=2[Cl:18])[C:7]#[N:8])=[CH:4][CH:3]=1.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.S([O-])([O-])(=O)=O.[Mg+2]>C(OC(=O)C)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH:6]([C:9]2[C:10]([Cl:18])=[CH:11][C:12]([NH:16][N:17]=[CH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:13][C:14]=2[Cl:15])[C:7]#[N:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 220085374-(4-Chloro-alpha-cyanobenzyl)-3,5-dichlorophenyl hydrazine

Product 1

HCID 86754869Benzaldehyde 4-(4-chloro-alpha-cyanobenzyl)-3,5-dichlorophenyl hydrazone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 30 ml of acetic acid ethyl ester was dissolved 3.26 g of 4-(4-chloro-α-cyanobenzyl)-3,5-dichlorophenyl hydrazine. To the solution was added equimolar benzaldehyde and three times as much mol. of anhydrous magnesium sulfate, then the reaction was allowed to proceed for one hour at room temperature. After completion of the reaction, insolubles were removed, and the solution was concentrated, which was recrystallized from acetonitrile to afford 3.3 g of the titled compound as colorless crystals, m.p.162-163° C.

Workup

  1. customAfter completion of the reaction, insolubles
  2. customwere removed
  3. concentrationthe solution was concentrated
  4. customwhich was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-1498695bf0a84033b1a6147d20c71936
Source dataset
uspto-grants-2001_04
Patent number
US06211178B1

Reaction notes

Loading…