تفاعل #464737

معادلة التفاعل

N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide

compound 8

N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide

sodium iodide

acetone

→

N-(3-chlorophenyl)-2-(2,3-dihydro-6-iodomethyl-4-oxo-5-phenyl-4H-2,3-oxazin-3-yl)-2-methylpropanamide

المذيبات

ether

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةunder reflux for 18 hours
3. 3
   أخرىevaporated
4. 4
   أخرىto give a residue which
5. 5
   غسيلThe ethereal solution was washed in turn with saturated aqueous sodium thiosulphate solution and water
6. 6
   تجفيفdried (magnesium sulphate)
7. 7
   أخرىevaporated under reduced pressure
8. 8
   أخرىto leave a residue which
9. 9
   أخرىwas purified
10. 10
    أخرىby dry column chromatography on silica
11. 11
    غسيلeluting with ethyl acetate/dichloromethane

الإجراء التجريبي

A mixture of N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 8, 0.2 g) and sodium iodide (0.065 g) in acetone was heated under reflux for 18 hours, then evaporated to give a residue which was redissolved in ether. The ethereal solution was washed in turn with saturated aqueous sodium thiosulphate solution and water, dried (magnesium sulphate) and evaporated under reduced pressure to leave a residue which was purified by dry column chromatography on silica, eluting with ethyl acetate/dichloromethane to give N-(3-chlorophenyl)-2-(2,3-dihydro-6-iodomethyl-4-oxo-5-phenyl-4H-2,3-oxazin-3-yl)-2-methylpropanamide (compound 9, 0.04 g) as a white solid, m.p. 134.6-136.6° C.

المصدر