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

HRID 377555
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HRID 377555 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:28])[C:10]([N:13]2[C:18](=[O:19])[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:16]([CH2:26]Br)OC2)([CH3:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.[I-:29].[Na+].C[C:32](C)=[O:33]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:28])[C:10]([N:13]2[C:18](=[O:19])[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:16]([CH2:26][I:29])[CH2:32][O:33]2)([CH3:11])[CH3:12])[CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 19354652N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide2회

생성물 1

HCID 70253527N-(3-chlorophenyl)-2-(2,3-dihydro-6-iodomethyl-4-oxo-5-phenyl-4H-2,3-oxazin-3-yl)-2-methylpropanamide

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customevaporated
  4. customto give a residue which
  5. washThe ethereal solution was washed in turn with saturated aqueous sodium thiosulphate solution and water
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated under reduced pressure
  8. customto leave a residue which
  9. customwas purified
  10. customby dry column chromatography on silica
  11. washeluting with ethyl acetate/dichloromethane

출처 및 근거

ORD 기록
ord-2d742cc0fdb5484c99a2a35976805918
출처 데이터셋
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06028032

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