Diphosgene → 8-Fluoroisatoic anhydride

HRID 1688096Notes

Reaction equation

HRID 1688096 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13]([O:16]C(Cl)=O)(Cl)Cl>C(Cl)Cl>[F:11][C:10]1[C:2]2[NH:1][C:13](=[O:16])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 5864082-Amino-3-fluorobenzoic acid

Product 1

HCID 105353938-Fluoroisatoic anhydrideYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-amino-3-fluoro-benzoic acid (2.3 g) in DCM (20 mL) was added trichloromethylchloroformate (3.0 g) and the mixture was stirred at rt for 16 hours. The reaction was then concentrated to provide 8-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (2.5 g).

Workup

  1. concentrationThe reaction was then concentrated

Sources & evidence

ORD record
ord-bbbcfb65271949639a3f7f409f831903
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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