Chloranil → 6-Nitro-2-(1,3-benzodioxole-5-yl)-quinazoline

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.

1. additionwas added at 0° C
2. customThe solvent was removed i.v
3. customand the residue triturated with ethanol/water 1/9
4. customThe obtained solid was dried
5. temperatureThe mixture was heated
6. temperatureat reflux for 2 hours
7. customthe solvent was removed i.v
8. customand the residue was triturated with water/ammonia
9. washwashed with water
10. dry with materialdried over P2O5
11. temperaturewas heated
12. temperatureat reflux for 2 hours
13. concentrationThe mixture was concentrated i.v
14. customand the residue was triturated with NaOH 1M
15. washwashed with water and with methanol
16. customThe obtained solid was dried i.v

ORD 기록

ord-808266bd50b44deb9e23ca3d7e66ac90

출처 데이터셋

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08193353B2