Benzaldehyde → 4H-3,1-Benzoxazin-4-one, 2,2'-(2-phenylethenylidene)bis-

HRID 845100Notes

Reaction equation

HRID 845100 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([C:21]1[O:26][C:25](=[O:27])[C:24]2[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=2[N:22]=1)[C:10]1[O:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]=1.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH:5]1[CH:6]=[CH:7][C:2]([CH:1]=[C:9]([C:10]2[O:15][C:14](=[O:16])[C:13]3[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:11]=2)[C:21]2[O:26][C:25](=[O:27])[C:24]3[C:23](=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:22]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 13650289HCID 13650289, compound

Product 1

HCID 30638134H-3,1-Benzoxazin-4-one, 2,2'-(2-phenylethenylidene)bis-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Benzaldehyde (259 mg, 2.45 mmol), Compound (2,2'-methylenebis(3,1-benzoxazine-4-one) (500 mg, 1.63 mmol), and BF3. (C2H5)2O (0.045 ml, 0.163 mmol) were heated under reflux in dry toluene (20 ml) for 20 hours. After the reaction, the solvent was removed under reduced pressure from the reaction mixture, the residue was treated with water, extracted with benzene, and the organic layer was separated, washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in the developing solvent and adsorbed on silica gel, and was purified by column chromatography to give the desired compound 52. The obtained product was crystallized from isopropylether to give the desired compound 52 in white solid in a good yield. m.p., IR, and NMR spectra of the product fully agreed with those of the one obtained in Example 19.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed under reduced pressure from the reaction mixture
  3. additionthe residue was treated with water
  4. extractionextracted with benzene
  5. customthe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. dissolutionThe residue was dissolved in the developing solvent
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-fbb00ec6feb4434ab0bceb8b4e3e0e82
Source dataset
uspto-grants-1988_07
Patent number
US04755506

Reaction notes

Loading…