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

HRID 620763Notes

Reaction equation

HRID 620763 reaction equation
O=[C:2]([NH:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=[O:27])[C:3](=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](O)=[O:10])=[O:5].C(OCC)(=O)C>CN(C=O)C.C1C=CC=CC=1>[CH:20]1[CH:19]=[CH:18][C:17]([CH:16]=[C:3]([C:4]2[O:5][C:9](=[O:10])[C:8]3[C:7](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:6]=2)[C:2]2[O:27][C:26](=[O:28])[C:25]3[C:24](=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:23]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 8857Ethyl Acetate2×HCID 3062455Benzoic acid, 2,2'-((1,3-dioxo-2-(phenylmethylene)-1,3-propanediyl)diimino)bis-

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent2×

Procedure

The compound 11 (4.0 g, 9.3 mmol) was mmol) was dropwise added under ice cooling. To the mixture, 8 drops of dry DMF was further added, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was removed, and the residue was extracted with chloroform. The extract was washed with 1N.HCl, saturated aqueous NaCl soluticn, 4% NaHCO3 aqueous solution, and saturated aqueous NaCl solution and dried over MgSO4. The solvent was evaporated to give a pale yellow solid. The resultant product was dissolved in a mixed solution of benzene:ethyl acetate=1:1 and applied on a silica gel column for chromatography (developing solvent, benzene:ethyl acetate - 1:1). After removing the solvent from the eluent containing 2,2'-phenylethenilidene-bis(3,1-benzoxazine-4-one) [Compound 52], the residue was crystallized from isopropyl ether to give the Compound 52 in white solid (3.0 g, yield, 82%), which was recrystallized from the mixed solvent of benzene and n-hexane to give white crystal (2.5 g, yield, 68%). m.p., 214°-215° C.

Workup

  1. additionwas dropwise added under ice cooling
  2. customAfter completion of the reaction
  3. customthe solvent was removed
  4. extractionthe residue was extracted with chloroform
  5. washThe extract was washed with 1N
  6. dry with materialHCl, saturated aqueous NaCl soluticn, 4% NaHCO3 aqueous solution, and saturated aqueous NaCl solution and dried over MgSO4
  7. customThe solvent was evaporated
  8. customto give a pale yellow solid
  9. customAfter removing the solvent from the eluent
  10. additioncontaining 2,2'-phenylethenilidene-bis(3,1-benzoxazine-4-one) [Compound 52]
  11. customthe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-34215d9b09d5401a8185ad64ba2779ce
Source dataset
uspto-grants-1989_04
Patent number
US04822791

Reaction notes

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