تفاعل #40583

معادلة التفاعل

calcium carbonate

benzyltrimethylammonium dichloroiodate

5-amino-2-chloropyridine

→

expected product

المردود 39.1%

3-Amino-6-chloro-2-iodopyridine

المردود 39.1%

المذيبات

methanol

dichloro-methane

ظروف التفاعل

المعالجة

1. 1
   ترشيحfiltered
2. 2
   أخرىto remove the mineral salts
3. 3
   workup.ADDITIONThe filtrate is diluted with water
4. 4
   استخلاصextracted with DCM
5. 5
   أخرىThe organic phase obtained
6. 6
   غسيلis washed with sodium chloride solution
7. 7
   تجفيفwith saturated sodium thiosulfate solution, dried over magnesium sulfate
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىAn oil is obtained
10. 10
    أخرىwhich is purified by chromatography on silica gel
11. 11
    غسيلeluting with a cyclohexane/ethyl acetate mixture (80/20

الإجراء التجريبي

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%).

المصدر