Phosgene → 6,7-Difluoroisatoic anhydride

HRID 542813Notes

Reaction equation

HRID 542813 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[F:16][C:12]1[C:13]([F:15])=[CH:14][C:6]2[NH:5][C:1](=[O:2])[O:9][C:8](=[O:10])[C:7]=2[CH:11]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 7359652-Amino-4,5-difluorobenzoic acid

Product 1

HCID 109324446,7-Difluoroisatoic anhydride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of phosgene (45 g) in toluene (160 ml) was added during 20 minutes to a stirred solution of 2-amino-4,5-difluorobenzoic acid (26 g) in aqueous sodium carbonate (20.7 g anhydrous sodium carbonate in 350 ml water), keeping the temperature below 40°. The mixture was stirred at room temperature for 15 hours. The solid product was collected by filtration, washed with water and dried to give the novel compound 6,7-difluoro-1H-3,1-benzoxazine-2,4-dione, m.p. 223°-226° (dec.).

Workup

  1. customthe temperature below 40°
  2. filtrationThe solid product was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ee7484dae505460e88354dcb0036fcd6
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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