Phosgene → Methyl 4-ethoxy-2-(isocyanatosulfonyl)benzoate

HRID 703045

Reaktionsgleichung

Reaktionsgleichung von HRID 703045
[NH2:1][S:2]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][CH3:17])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3].C(N=[C:23]=[O:24])CCC.C(Cl)(Cl)=O>>[CH2:16]([O:15][C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([S:2]([N:1]=[C:23]=[O:24])(=[O:3])=[O:4])[CH:14]=1)[CH3:17]

Komponenten

4

Edukt 3

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 13987872Methyl 2-(aminosulfonyl)-4-ethoxybenzoate

Produkt 1

HCID 13987873Methyl 4-ethoxy-2-(isocyanatosulfonyl)benzoateAusbeute 98,4 %

Versuchsvorschrift

A solution of methyl 2-(aminosulfonyl)-4-ethoxybenzoate (7.56 g. 29.2 mmol). n-butyl isocyanate (3.29 mL. 29.2 mmol). and 1.4-diaza[2.2.2]bicyclooctane (0.13 g 1.2 mmol) in mixed xylenes was heated at reflux for 10 minutes. Phosgene was then added at such a rate that the internal temperature stayed at 133° C. or above. When consumption of phosgene ceased, the solution was cooled to room temperature and then filtered under nitrogen. Rotary evaporation gave methyl 4-ethoxy-2-(isocyanatosulfonyl)benzoate as a cloudy yellow oil (8.2 g). This was used immediately without further purification or characterization.

Aufarbeitung

  1. temperatureat reflux for 10 minutes
  2. customstayed at 133° C. or above
  3. customWhen consumption of phosgene
  4. filtrationfiltered under nitrogen
  5. customRotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-395aae7db70c45e1850be94acd1d7640
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04981509

Verknüpfte Notizen

Wird geladen…