Diphosgene → 5-Chloroisatoic anhydride

HRID 1767512Notes

Reaction equation

HRID 1767512 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[NH2:9][C:10]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>O1CCOCC1>[Cl: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 124762-Amino-5-chlorobenzoic acid

Product 1

HCID 784805-Chloroisatoic anhydrideYield 92.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Trichloromethyl chloroformate (4.8 mL, 300 mmol) was added to a stirred solution of Compound 57 (6.84 g, 40 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 7.3 g (92%) of white solids. 1H NMR (DMSO-d6): δ 7.47 (d, J=8.6 Hz, 1H), 7.70 (dd, J=8.6, 1.8 Hz, 1H), 7.82 (d, J=1.1, 1H), 11.63 (s, 1H).

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-b3031ddb460043cba293a68c157e1742
Source dataset
uspto-grants-2007_06
Patent number
US07235546B2

Reaction notes

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