反应 #2510190

反应方程式

dimethylformamide

chloroform

6,7-diacetoxy-4(3H)-quinazolinone

Thionyl chloride

→

N-(3-ethynylphenyl)-6,7-diacetoxy-4-quinazolinamine hydrochloride

收率 73.6%

反应条件

后处理

1. 1
   其他Into a 3.0 Lt four necked round bottomed flask, equipped with a mechanical stirrer
2. 2
   温度reflux condenser
3. 3
   workup.ADDITIONaddition funnel
4. 4
   其他obtained from the process
5. 5
   温度The reaction mass was slowly heated
6. 6
   温度to reflux temperature
7. 7
   温度maintained
8. 8
   温度at reflux temperature for 6 hours
9. 9
   其他Reaction
10. 10
    workup.DISTILLATIONadded chloroform (500 ml) and distilled out 500 ml of chloroform
11. 11
    温度Then cooled the reaction mass to 20° C
12. 12
    workup.ADDITION3-Ethynylaniline (15 g) was added
13. 13
    温度maintained for 2-3 hours at 20-25° C
14. 14
    workup.DISTILLATIONDistilled of the solvent completely under vacuum
15. 15
    温度Cooled the reaction mass to 20-25° C.
16. 16
    其他triturated with isopropyl alcohol
17. 17
    过滤filtered
18. 18
    洗涤washed the cake with isopropyl alcohol
19. 19
    其他dried

实验过程

Into a 3.0 Lt four necked round bottomed flask, equipped with a mechanical stirrer, reflux condenser, pressure equalizing addition funnel and thermometer socket are charged chloroform (500 ml), 6,7-diacetoxy-4(3H)-quinazolinone (25 g) obtained from the process described in step (ii) of example (1) and dimethylformamide (3 ml). Thionyl chloride (46.2 g) was slowly added in about 20-30 minutes. The reaction mass was slowly heated to reflux temperature and maintained at reflux temperature for 6 hours. Reaction was found to be over by HPLC. Cooled to 45-50° C. then added chloroform (500 ml) and distilled out 500 ml of chloroform. Repeated the distillation process another two times with fresh chloroform. Then cooled the reaction mass to 20° C. 3-Ethynylaniline (15 g) was added and maintained for 2-3 hours at 20-25° C. Completion of the reaction is monitored by HPLC. Distilled of the solvent completely under vacuum. Cooled the reaction mass to 20-25° C. and triturated with isopropyl alcohol and filtered and washed the cake with isopropyl alcohol and dried to get N-(3-ethynylphenyl)-6,7-diacetoxy-4-quinazolinamine hydrochloride 28 g (73.6% by theory).

来源