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

HRID 620766Notes

Reaction equation

HRID 620766 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(Cl)(=O)C(Cl)=O>C1C=CC=CC=1.CN(C=O)C>[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 65578Oxalyl chlorideHCID 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 241BenzeneSolvent

Procedure

The Compound 11 (4 g, 9.28 mmol) was suspended in dry benzene (100 ml) and oxalyl chloride (3.2 ml, 37.18 mmol) was added dropwise under ice cooling. Then, with addition cf 8 drops of dry DMF, the mixture was stirred at room temperature for 2 hours. After the reaction, the solvent was removed and the residue was extracted with chloroform. The organic layer was washed with 1N.HCl, saturated brine, 4% NaHCO3 aqueous solution, and saturated brine and dried over magnesium sulfate. The solvent was evaporated. The residue was dissolved in chlcroform and applied on silica gel column for chromatography (benzene ethyl acetate=4:1). Recrystallization from isopropyl ether gave the desired compound 52 in crystal (3.26 g, yield, 89%). m.p., IR, and NMR pectra of the product fully agreed with those of the one obtained in Example 19.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed
  3. extractionthe residue was extracted with chloroform
  4. washThe organic layer was washed with 1N
  5. dry with materialHCl, saturated brine, 4% NaHCO3 aqueous solution, and saturated brine and dried over magnesium sulfate
  6. customThe solvent was evaporated
  7. dissolutionThe residue was dissolved in chlcroform
  8. customRecrystallization from isopropyl ether

Sources & evidence

ORD record
ord-e289c18fcd1c4a6084471e8c488215e2
Source dataset
uspto-grants-1989_04
Patent number
US04822791

Reaction notes

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