Phosgene → 8-fluoro-6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 2234631Notes

Reaction equation

HRID 2234631 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](Cl)(Cl)=[O:14]>O1CCCC1.C1(C)C=CC=CC=1>[F:11][C:10]1[C:2]2[NH:1][C:13](=[O:14])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=[C:8]([I:12])[CH:9]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 577314632-Amino-3-fluoro-5-iodobenzoic acid

Product 1

HCID 577315858-fluoro-6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 500 mg (1.78 mmol) of 2-amino-3-fluoro-5-iodo-benzoic acid in 5.0 mL tetrahydrofuran was added 1.4 mL (2.67 mmol) of 20% w/v solution of phosgene in toluene. The reaction was stirred for 16 hours at room temperature. The solution was concentrated to dryness to afford 550 mg (1.79 mmol, quantitative yield) of 8-fluoro-6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione as a brown powder. 1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.09 (dd, 1H), 7.98 (s, 1H).

Workup

  1. concentrationThe solution was concentrated to dryness

Sources & evidence

ORD record
ord-3b5af9645674468a9ac713cc0de92070
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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