Phosgene → 5-Fluoroisatoic anhydride

HRID 1816261Notes

Reaction equation

HRID 1816261 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](Cl)(Cl)=[O:13]>[OH-].[Na+].C1(C)C=CC=CC=1>[F:11][C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:12](=[O:13])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 2885605-Fluoroisatoic anhydride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-5-fluorobenzoic acid (1.91 g, 12.3 mmol) was dissolved in 1N sodium hydroxide solution (15 mL) and cooled to 0° C. under a nitrogen atmosphere. Phosgene (10 mL of a 20% solution in toluene) was added dropwise. After the addition was complete, the thick slurry was allowed to warm to room temperature. The precipitate was filtered off and rinsed with deionized water (2×50 mL). The precipitate was slurried in diethyl ether (50 mL), filtered, and dried under reduced pressure to yield 2.04 g of 6-fluoro-2H-3,1-benzoxazine-2,4(1H)-dione.

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. filtrationThe precipitate was filtered off
  4. washrinsed with deionized water (2×50 mL)
  5. filtrationfiltered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-0bf53d0d0807430e8825f4eb5e91a207
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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