Phosgene → 8-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 635515Notes

Reaction equation

HRID 635515 reaction equation
C[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([OH:10])=[O:9].[C:12](Cl)(Cl)=[O:13].[O:16]1CCOC[CH2:17]1>C1(C)C=CC=CC=1>[CH3:17][O:16][C:5]1[CH:4]=[CH:3][CH:2]=[C:7]2[C:8]([O:10][C:12](=[O:13])[NH:11][C:6]=12)=[O:9]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 312751,4-DioxaneHCID 1512106-Methylanthranilic acid

Product 1

HCID 105596798-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 10.0 g (66.0 mmol) of 6-methylanthranilic acid in 60 mL of 1,4-dioxane was slowly added 100 mL (193 mmol) of a 1.93 molar solution of phosgene in toluene, at room temperature. The mixture was stirred overnight. The mixture was concentrated to yield a residue which was triturated with ethyl acetate-hexane (1:4), filtered, washed with hexane and dried to afford 11.579 (98.7%) of the 3-methoxyisatoic anhydride as a light brown solid. MS (Cl mode) m/z 160 (M-18,100%),178 (M+H, 95%).

Workup

  1. customat room temperature
  2. concentrationThe mixture was concentrated
  3. customto yield a residue which
  4. customwas triturated with ethyl acetate-hexane (1:4)
  5. filtrationfiltered
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-615788de9fc54d2389d088685e254b80
Source dataset
uspto-grants-2001_02
Patent number
US06187923B1

Reaction notes

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