Diphosgene → 5-Methylisatoic anhydride

HRID 346583

Reaction equation

HRID 346583 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[NH2:9][C:10]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>O1CCOCC1>[CH3:19][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 762552-Amino-5-methylbenzoic acid

Product 1

HCID 2944785-Methylisatoic anhydrideYield 94.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Trichloromethyl chloroformate (36.27 mL, 300 mmol) was added to a stirred solution of Compound 10 (41.3 g, 273 mmol) in dry dioxane at room temperature and the solution was refluxed for 4 h. The solution was cooled in ice bath and the solids formed were filtered. The solids were washed by ether and dried under vacuum at room temperature to yield 45.5 g (94%) of white solids. M.P. 257° C. 1H NMR (DMSO-d6): δ 2.32 (s, 3H), 7.06 (d, J=8.6 Hz, 1H), 7.56 (dd, J=8.6, 1.8 Hz, 1H), 7.71 (d, J=1.1, 1H), 11.63 (s, 1H). EIMS (neg. mode) m/z 176 (M−1), 152 (M+23). Anal. (C9H7NO3) C, H, N.

Workup

  1. temperaturethe solution was refluxed for 4 h
  2. temperatureThe solution was cooled in 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-6d6648e82c574ae48b32403967abf004
Source dataset
uspto-grants-2007_02
Patent number
US07173036B2

Linked notes

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