Benzaldehyde → Benzoic acid, 2,2'-((1,3-dioxo-2-(phenylmethylene)-1,3-propanediyl)diimino)bis-

HRID 845096Notes

Reaction equation

HRID 845096 reaction equation
[O:1]=[C:2]([NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20])[CH2:3][C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=[O:5].[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>N1C=CC=CC=1>[O:5]=[C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])[C:3](=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:2]([NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20])=[O:1]

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 130175852,2'-[(1,3-Dioxopropane-1,3-diyl)diazanediyl]dibenzoic acid

Product 1

HCID 3062455Benzoic acid, 2,2'-((1,3-dioxo-2-(phenylmethylene)-1,3-propanediyl)diimino)bis-Yield 54.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,2'-[(1,3-Dioxo-1,3-propanediyl)diimino]bisbenzoic acid (1.0 g) and benzaldehyde (0.46 g, 1.5 mol equivalent) were heated under reflux in dry pyridine (8 ml) for 16 hours. After removing pyridine, the mixture was treated with water, made alkaline with 10% aqueous ammonia under ice cooling, and the aqueous layer was washed with ether. The aqueous layer was made acidic (pH=2) with 1N HCl, and the precipitated crystals were collected by filtration. After washing with water, the resulting solid was purified by dissolving in tetrahydrofuran, adsorbing on the silica gel column and separating the desired compound using a developing solvent [ethyl acetate:benzene=1:1 (containing 1% acetic acid)]. After removing the initially eluted impurities, the solvent was removed from the effluent out liquid containing the desired compound. The residue was crystallized by adding water, collected on a filter, washed with water, and dried to give the title compound (0.686 g, yield, 51%), which was recrystallized from the mixed solvent of CH3OH--H2O system to obtain pale yellow crystals of monohydrate (Crystal a, 0.507 g) (Drying: 1 mm Hg, 100° C., 15 hours), m.p., 195°-196° C.

Workup

  1. customAfter removing pyridine
  2. additionthe mixture was treated with water
  3. washthe aqueous layer was washed with ether
  4. filtrationthe precipitated crystals were collected by filtration
  5. washAfter washing with water
  6. customthe resulting solid was purified
  7. dissolutionby dissolving in tetrahydrofuran
  8. customseparating the desired compound
  9. additiona developing solvent [ethyl acetate:benzene=1:1 (containing 1% acetic acid)]
  10. customAfter removing the initially eluted impurities
  11. customthe solvent was removed from the effluent out liquid
  12. additioncontaining the desired compound
  13. customThe residue was crystallized
  14. additionby adding water
  15. customcollected on a filter
  16. washwashed with water
  17. customdried

Sources & evidence

ORD record
ord-6d7a995ad89346f4bc8f3762c23d55e5
Source dataset
uspto-grants-1988_07
Patent number
US04755506

Reaction notes

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