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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
ノート
印刷プレビュー

反応式

HRID 377555 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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-methylpropanamide2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2d742cc0fdb5484c99a2a35976805918
出典データセット
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06028032

反応ノート

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