Diphosgene → 5-Methylisatoic anhydride

HRID 346583

Reaktionsgleichung

Reaktionsgleichung von HRID 346583
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

Komponenten

4

Edukt 2

HCID 10426DiphosgeneHCID 762552-Amino-5-methylbenzoic acid

Produkt 1

HCID 2944785-Methylisatoic anhydrideAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6d6648e82c574ae48b32403967abf004
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173036B2

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