Propylamine → Proquinazid

HRID 1276616

Reaktionsgleichung

Reaktionsgleichung von HRID 1276616
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]([O:15][CH2:16][CH2:17][CH3:18])=S)=[C:6]([CH:11]=1)[C:7]([O:9]C)=O.[CH2:19]([NH2:22])[CH2:20][CH3:21]>>[I:1][C:2]1[CH:11]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:12]=[C:13]([O:15][CH2:16][CH2:17][CH3:18])[N:22]([CH2:19][CH2:20][CH3:21])[C:7]2=[O:9]

Komponenten

3

Edukt 2

HCID 7852PropylamineHCID 22116535Methyl 5-iodo-2-[(propoxythioxomethyl)amino]benzoate

Produkt 1

HCID 11057771Proquinazid

Versuchsvorschrift

To the remaining 320 mL solution of methyl 5-iodo-2-[(propoxythioxomethyl)amino]benzoate from Step C above was added 10.86 mL (0.132 mol) of propylamine. The reaction solution was heated at reflux overnight, concentrated to 1/3 volume under reduced pressure, and treated with 75 mL water added dropwise at room temperature. Following refrigeration at 0-5° C. overnight, an additional 25 mL H2O was added and cooling was continued for an additional 48 h. Filtration of the ensuing mixture provided 15.68 g of the title compound, 1H NMR (300 MHz, CDCl3): δ0.96 (t,3H); 1.06 (t,3H); 1.64-1.79 (m,2H); 1.81-1.92 (m,2H); 4.05 (t,2H); 4.43 (t,2H); 7.19 (d,1H); 7.85 (dd,1H); 8.49 (d,1H), m.p. 49-53° C.

Aufarbeitung

  1. temperatureThe reaction solution was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated to 1/3 volume under reduced pressure
  4. additiontreated with 75 mL water
  5. additionadded dropwise at room temperature
  6. customat 0-5° C.
  7. customovernight
  8. additionan additional 25 mL H2O was added
  9. temperaturecooling
  10. filtrationFiltration of the ensuing mixture

Quellen und Nachweise

ORD-Eintrag
ord-ec4a9596d09c42a0a536ad063ae44824
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06166208

Verknüpfte Notizen

Wird geladen…