반응 #8444

반응 방정식

Pyridine

N-ethyldiisopropylamine

oxalyl chloride

aminobenzothiazole

water

water

Dimethylformamide

→

N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-2-methyl-isonicotinamide

용매

dichloromethane

반응 조건

후처리

1. 1
   세척The dropping funnel was rinsed with 4 ml dichloromethane
2. 2
   workup.ADDITIONThen 200 ml tetrahydrofuran were added
3. 3
   기타to partially precipitate
4. 4
   workup.WAITAfter 0.2 h
5. 5
   workup.STIRRINGthe reaction mixture was stirred at RT overnight (˜17 h)
6. 6
   온도The contents were heated
7. 7
   workup.ADDITIONwere added
8. 8
   온도whilst maintaining ca. constant volume throughout a distillation process until the internal temperature
9. 9
   기타reached 90° C
10. 10
    온도heating
11. 11
    온도was increased to 110° C.
12. 12
    workup.DISTILLATIONa total of 280 ml of distillate was collected
13. 13
    workup.ADDITIONA further 320 ml water was added in one portion
14. 14
    온도the temperature was increased to 120° C. whereby the internal and distillate temperature
15. 15
    기타rose to ˜70° C.

실험 절차

20.0 g Pyridine acid (115 mmol) were suspended at RT in 100 ml dichloromethane. 0.5 ml Dimethylformamide (6.5 mmol) was added, and after 0.2 h, 14.9 g oxalyl chloride (10.2 ml, 115 mmol) were added over 2 min. The dropping funnel was rinsed with 4 ml dichloromethane. The brown suspension was stirred at RT for 3 h. Then 200 ml tetrahydrofuran were added causing the acid chloride to partially precipitate. After 0.2 h, 24.3 g aminobenzothiazole (IA) (92 mmol) were added in one portion at RT. Directly afterwards, 56.0 ml N-ethyldiisopropylamine (42 g, 321 mmol) were added over 0.1 h., and the reaction mixture was stirred at RT overnight (˜17 h). The contents were heated to reflux (˜60° C.), and 300 ml water were added whilst maintaining ca. constant volume throughout a distillation process until the internal temperature reached 90° C. Once all the water was added, heating was increased to 110° C. and a total of 280 ml of distillate was collected. A further 320 ml water was added in one portion, and the temperature was increased to 120° C. whereby the internal and distillate temperature rose to ˜70° C.

출처