Benzaldehyde → N'-benzylidene-4-trifluoromethylbenzohydrazide

HRID 1354412Notes

Reaction equation

HRID 1354412 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][NH2:10])=[O:8])=[CH:5][CH:4]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S(=O)(=O)(O)O>CO>[CH:15](=[N:10][NH:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([C:2]([F:13])([F:14])[F:1])=[CH:4][CH:5]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 1118Sulfuric AcidHCID 5206624-(Trifluoromethyl)benzohydrazide

Product 1

HCID 6736306N'-benzylidene-4-trifluoromethylbenzohydrazideYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (50 ml) of 4-trifluoromethylbenzohydrazide (3.06 g) and benzaldehyde (1.52 ml) in methanol was added dropwise conc. sulfuric acid (0.5 ml), and this mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the residue was washed with hexane-ethanol (1:1, volume ratio) and recrystallized from ethanol to give N′-benzylidene-4-trifluoromethylbenzohydrazide (3.23 g, yield 74%) as colorless needle crystals. melting point: 216–217° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with hexane-ethanol (1:1, volume ratio)
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-04360be69d8a45b491ff0ea21c329994
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

Loading…