Isatoic Anhydride → HCID 103821981, compound

HRID 523208Notes

Reaction equation

HRID 523208 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=O)[O:3]C1=O.[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>CN(C=O)C.O>[NH2:1][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]([NH:17][C:16]1[CH:18]=[CH:19][CH:20]=[C:14]([Br:13])[C:15]=1[CH3:21])=[O:3]

Participants

5

Reactant 2

HCID 8359Isatoic AnhydrideHCID 1235383-Bromo-o-toluidine

Product 1

HCID 103821981HCID 103821981, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 1H-benzo[d][1,3]oxazine-2,4-dione (10.00 g, 61.3 mmol) in DMF (150 mL) was treated with 3-bromo-2-methylaniline (13.69 g, 73.6 mmol) and heated to reflux overnight. The cooled mixture was diluted with water and extracted with EtOAc. The whole mixture was filtered to remove grey solids and the layers of the filtrate were separated. The organic phase was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (330 g), eluting with EtOAc-hexanes (gradient from 0-50%), to give 2-amino-N-(3-bromo-2-methylphenyl)benzamide as tan solid (1.1 g, 6% yield). A second eluent from the column gave 3-(3-bromo-2-methylphenyl)quinazoline-2,4(1H,3H)-dione [Intermediate 4B] as a tan solid (3.4 g, 17% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. extractionextracted with EtOAc
  4. filtrationThe whole mixture was filtered
  5. customto remove grey solids
  6. customthe layers of the filtrate were separated
  7. washThe organic phase was washed with water
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography on silica gel (330 g)
  11. washeluting with EtOAc-hexanes (gradient from 0-50%)

Sources & evidence

ORD record
ord-77652ad0099a4bf9b38c1ff36bb8d50b
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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