반응 #40583

반응 방정식

calcium carbonate

benzyltrimethylammonium dichloroiodate

5-amino-2-chloropyridine

→

expected product

수율 39.1%

3-Amino-6-chloro-2-iodopyridine

수율 39.1%

용매

methanol

dichloro-methane

반응 조건

후처리

1. 1
   여과filtered
2. 2
   기타to remove the mineral salts
3. 3
   workup.ADDITIONThe filtrate is diluted with water
4. 4
   추출extracted with DCM
5. 5
   기타The organic phase obtained
6. 6
   세척is washed with sodium chloride solution
7. 7
   건조with saturated sodium thiosulfate solution, dried over magnesium sulfate
8. 8
   농축concentrated under reduced pressure
9. 9
   기타An oil is obtained
10. 10
    기타which is purified by chromatography on silica gel
11. 11
    세척eluting with a cyclohexane/ethyl acetate mixture (80/20

실험 절차

23.2 g (180.5 mM) of 5-amino-2-chloropyridine are mixed in 70 ml of dichloro-methane (DCM) and 180 ml of methanol, and 21.6 g (216 mM) of calcium carbonate and 75.3 g (226 mM) of benzyltrimethylammonium dichloroiodate are added. The reaction mixture is stirred at room temperature for 16 hours, and then filtered to remove the mineral salts. The filtrate is diluted with water and extracted with DCM. The organic phase obtained is washed with sodium chloride solution, and then with saturated sodium thiosulfate solution, dried over magnesium sulfate and concentrated under reduced pressure. An oil is obtained, which is purified by chromatography on silica gel, eluting with a cyclohexane/ethyl acetate mixture (80/20 and then 70/30; v/v). 13.9 g of the expected product are thus obtained in the form of an orange-colored solid (yield=30%).

출처