Chloroform → HCID 54386067, compound

HRID 1196844Notes

Reaction equation

HRID 1196844 reaction equation
[O:1]=[C:2]([C:10]1[CH:20]=[CH:19][C:13]2[NH:14][C:15](=O)[CH2:16][O:17][C:12]=2[CH:11]=1)[CH:3]([CH3:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].C(Cl)(Cl)Cl.O=P(Cl)(Cl)[Cl:27].[CH3:30][N:31]([CH3:34])[CH:32]=O>>[O:1]=[C:2]([C:10]1[CH:20]=[CH:19][C:13]2[N:14]=[C:15]([Cl:27])[C:16](=[CH:30][N:31]([CH3:34])[CH3:32])[O:17][C:12]=2[CH:11]=1)[CH:3]([CH3:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 19896706HCID 19896706, compound

Product 1

HCID 54386067HCID 54386067, compound

Procedure

Methyl 4-oxo-4-(3,4-dihydro-3-oxo-2H-1,4-benzoxazin-7-yl)-3-methylbutyrate (10 g) was added to chloroform (100 ml) containing POCl3 (3.5 ml) and dimethylformamide (2.8 ml) at 0° C. The mixture was heated at reflux for 3 hours then stirred at room temperature overnight. The solvent was removed at reduced pressure, the residue was basified with 10% NaOH solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated to dryness. The residue was chromatographed on silica gel and eluted with methylene chloride. The fractions containing the Product were evaporated to dryness and the residue used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was removed at reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was chromatographed on silica gel
  10. washeluted with methylene chloride
  11. additionThe fractions containing the Product
  12. customwere evaporated to dryness
  13. customthe residue used without further purification

Sources & evidence

ORD record
ord-3448d9168f834ffeb6b2af6daad82c4d
Source dataset
uspto-grants-1992_05
Patent number
US05116837

Reaction notes

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