4-Bromoisatoic anhydride → HCID 178418391, compound

HRID 3121

Reaction equation

HRID 3121 reaction equation
[Na].O=[C:3]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Br:15][C:16]1[CH:27]=[CH:26][C:19]2[C:20](=O)[O:21]C(=O)[NH:23][C:18]=2[CH:17]=1>CN(C)C=O>[Br:15][C:16]1[CH:17]=[C:18]2[C:19]([C:20]([OH:21])=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N:23]2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 115215774-Bromoisatoic anhydrideHCID 57351814Diethyl 2-oxosuccinate,sodium salt

Product 1

HCID 178418391HCID 178418391, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
130 °C

Procedure

To a stirred mixture of diethyl oxosuccinate sodium salt (1.31 g, 6.23 mM) in dimethylformamide (DMF, 15 mL) under a nitrogen atmosphere was added a solution of 7-bromo-2H-3,1-benzoxazine-2,4(1H)-dione (1.50 g, 6.20 mM) in DMF (15 mL). The resulting reaction mixture was heated to 130° C. over 2.5 hr and then refluxed for 5 hr. After cooling to room temperature, the reaction mixture was concentrated and the residue was chromatographed over silica gel (eluant: ethyl acetate/methylene chloride; 5/95). The fractions containing the desired material were combined and concentrated. The solid residue was recrystallized from ethanol/ether to provide (0.54 g, 24%) the title compound as a tan solid, mp 233.5°-234.5° C.; MS(CI): 368, 369 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. temperaturerefluxed for 5 hr
  3. temperatureAfter cooling to room temperature
  4. concentrationthe reaction mixture was concentrated
  5. customthe residue was chromatographed over silica gel (eluant: ethyl acetate/methylene chloride; 5/95)
  6. additionThe fractions containing the desired material
  7. concentrationconcentrated
  8. customThe solid residue was recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-ec04a768a81546c687358bb4525e5d24
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Linked notes

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