Reaktion #304319

Reaktionsgleichung

chloranil

5-nitro-2-amino-benzylamine hydrochloride

piperonyloyl chloride

→

6-nitro-2-(1,3-benzodioxol-5-yl)-quinazoline

Ausbeute 82.5%

Lösungsmittel

DCM

toluene

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at 0° C
2. 2
   SonstigeThe solvent was removed i.v
3. 3
   Sonstigeand the residue triturated with ethanol/water 1/9
4. 4
   SonstigeThe obtained solid was dried
5. 5
   TemperaturThe mixture was heated
6. 6
   Temperaturat reflux for 2 hours
7. 7
   Sonstigethe solvent was removed i.v
8. 8
   Sonstigeand the residue was triturated with water/ammonia
9. 9
   Waschenwashed with water
10. 10
    Trocknendried over P2O5
11. 11
    Temperaturwas heated
12. 12
    Temperaturat reflux for 2 hours
13. 13
    EinengenThe mixture was concentrated i.v
14. 14
    Sonstigeand the residue was triturated with NaOH 1M
15. 15
    Waschenwashed with water and with methanol
16. 16
    SonstigeThe obtained solid was dried i.v

Vorschrift

To a suspension of 5-nitro-2-amino-benzylamine hydrochloride (31 g, 0.152 mol) in DCM (450 ml) was added at 0° C. TEA (52.6 ml, 0.38 mol) and a solution of piperonyloyl chloride (27.3 g, 0.16 mol) in DCM (80 ml). The mixture was stirred for 2 hours at r.t. The solvent was removed i.v. and the residue triturated with ethanol/water 1/9, then with diisopropyl ether. The obtained solid was dried and suspended in toluene (900 ml) and POCl3 (670 ml). The mixture was heated at reflux for 2 hours, then the solvent was removed i.v. and the residue was triturated with water/ammonia, washed with water, dried over P2O5. A mixture of the obtained product and chloranil (32.7 g, 0.129 mol) in toluene (500 ml) was heated at reflux for 2 hours. The mixture was concentrated i.v. and the residue was triturated with NaOH 1M, washed with water and with methanol. The obtained solid was dried i.v. (37 g, 82.5% yield). C15H9N3O4, MW: 295.26, mp 220-222° C.

Quelle