Реакция #304319

Уравнение реакции

chloranil

5-nitro-2-amino-benzylamine hydrochloride

piperonyloyl chloride

→

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

Выход 82.5%

Растворители

DCM

toluene

DCM

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added at 0° C
2. 2
   ДругоеThe solvent was removed i.v
3. 3
   Другоеand the residue triturated with ethanol/water 1/9
4. 4
   ДругоеThe obtained solid was dried
5. 5
   ТемператураThe mixture was heated
6. 6
   Температураat reflux for 2 hours
7. 7
   Другоеthe solvent was removed i.v
8. 8
   Другоеand the residue was triturated with water/ammonia
9. 9
   Промывкаwashed with water
10. 10
    Сушкаdried over P2O5
11. 11
    Температураwas heated
12. 12
    Температураat reflux for 2 hours
13. 13
    КонцентрированиеThe mixture was concentrated i.v
14. 14
    Другоеand the residue was triturated with NaOH 1M
15. 15
    Промывкаwashed with water and with methanol
16. 16
    ДругоеThe obtained solid was dried i.v

Методика

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.

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