4H-3,1-Benzoxazin-4-one, 2,2'-(2-phenylethenylidene)bis- → Benzoic acid, 2,2'-((1,3-dioxo-2-(phenylmethylene)-1,3-propanediyl)diimino)bis-, bis(1,1-dimethylethyl) ester

HRID 845099Notes

Reaction equation

HRID 845099 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]=[C:8]([C:20]2[O:30][C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)[C:9]2[O:19][C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:3][CH:2]=1.[O:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[K]>C1C=CC=CC=1.C(Cl)(Cl)Cl>[O:19]=[C:9]([NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=1[C:17]([O:31][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:18])[C:8](=[CH:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[C:20]([NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=1[C:28]([O:31][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])=[O:30]

Participants

5

Reactant 2

HCID 30638134H-3,1-Benzoxazin-4-one, 2,2'-(2-phenylethenylidene)bis-HCID 178418922HCID 178418922, compound

Product 1

HCID 3063814Benzoic acid, 2,2'-((1,3-dioxo-2-(phenylmethylene)-1,3-propanediyl)diimino)bis-, bis(1,1-dimethylethyl) esterYield 59%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Procedure

The compound 52 (1.0 g, 2.5 mmol) obtained in the same manner as in Example 21 (b) was dissolved in dry benzene (80 ml), treated with KOC(CH3)3 (684 mg, 6.1 mmol), and heated under reflux for 1 hour. After completion of the reaction, the solvent was evaporated and the residue was dried and suspended by adding a small amount of water under ice cooling. The aqueous layer was made neutral with 0.5N.HCl, and the residue was dissolved by adding chloroform. The mixed layer was removed to a separating funnel. After the solid was completely dissolved, water was added to wash the solution so as to make the chloroform layer neutral or weak acidic. The chloroform layer was separated, washed with saturated aqueous NaCl solution and dried over magnesium sulfate. The solvent was evaporated to give a white solid. The product was dissolved in chloroform and purified by silica gel column chromatography (developing solvent: benzene:ethyl acetate=4:1) to give the desired compound as white solid (801 mg, crude yield 58%). Recrystallization from the mixed solvent of methanol and water gave white crystals (654 mg, yield, 47%). m.p., 117°-118° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated
  5. customthe residue was dried
  6. additionby adding a small amount of water under ice cooling
  7. dissolutionHCl, and the residue was dissolved
  8. additionby adding chloroform
  9. customThe mixed layer was removed to a separating funnel
  10. dissolutionAfter the solid was completely dissolved
  11. additionwater was added
  12. washto wash the solution so as
  13. customThe chloroform layer was separated
  14. washwashed with saturated aqueous NaCl solution
  15. dry with materialdried over magnesium sulfate
  16. customThe solvent was evaporated
  17. customto give a white solid
  18. custompurified by silica gel column chromatography (developing solvent: benzene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1b86eeb0d09046d0a76da8c1cc656fdf
Source dataset
uspto-grants-1988_07
Patent number
US04755506

Reaction notes

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