Diphosgene → 5-Chloro-3-methyl isatoic anhydride

HRID 475470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475470
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:14](OC(Cl)(Cl)Cl)=[O:15]>O1CCOCC1>[Cl:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:2]2[NH:1][C:14](=[O:15])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Komponenten

4

Edukt 2

HCID 10426DiphosgeneHCID 116440442-Amino-5-chloro-3-methylbenzoic acid

Produkt 1

HCID 115502595-Chloro-3-methyl isatoic anhydride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
42 °C

Versuchsvorschrift

To a suspension of 2-amino-3-methyl-5-chlorobenzoic acid (i.e. product of Example 6, Step A) (97 g, 520 mmol) stirred, in dry dioxane (750 mL) at room temperature, trichloromethyl chloroformate (63 g, 320 mmol) was added dropwise. The reaction mixture exothermically warmed slowly to 42° C., and the solid almost completely dissolved before a thick suspension formed again. After the suspension was stirred at ambient temperature for 2.5 hours, the title compound was isolated by filtration, washed with ethyl ether, and dried to yield the title product compound, obtained as a white solid (98 g). 1H NMR (DMSO-d6) δ 2.3 (s, 3H), 7.70 (s, 1H), 7.75 (s, 1H), 11.2 (s, 1H).

Aufarbeitung

  1. dissolutionthe solid almost completely dissolved before a thick suspension
  2. customformed again

Quellen und Nachweise

ORD-Eintrag
ord-71f81ca5afcb460a8ee03d0c130e609a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637552B2

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