Diphosgene → 5-Fluoroisatoic anhydride

HRID 346605Notes

Reaction equation

HRID 346605 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[NH2:9][C:10]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>O1CCOCC1>[F:19][C:16]1[CH:17]=[CH:18][C:10]2[NH:9][C:2](=[O:3])[O:13][C:12](=[O:14])[C:11]=2[CH:15]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 2885605-Fluoroisatoic anhydrideYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Trichloromethyl chloroformate (7.01 mL, 58.13 mmol) was added to a stirred solution of Compound 34 (8.2 g, 52.85 mmol) in dry dioxane at room temperature and the solution was refluxed for 4 h. The solution was cooled in an ice bath and the solids formed were filtered. The solids were washed by ether and dried under vacuum at room temperature to yield 9.1 g (96%) of white solids. M.P. 240° C. 1H NMR (DMSO-d6): δ 7.19 (dd, J=4.2, 8.9 Hz, 1H), 7.63–7.71 (m, 1H), 11.77 (s, 1H). EIMS (neg. mode) m/z 180 (M−1). Anal. (C8H4FNO3) C, H, N.

Workup

  1. temperaturethe solution was refluxed for 4 h
  2. temperatureThe solution was cooled in an ice bath
  3. customthe solids formed
  4. filtrationwere filtered
  5. washThe solids were washed by ether
  6. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-ebf5046ab18349a39818fceadecc5e8f
Source dataset
uspto-grants-2007_02
Patent number
US07173036B2

Reaction notes

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