Methanol → N-[4-(1,3-dioxolyl)phenyl]isatin

HRID 1431915

反応式

HRID 1431915 の反応式
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].[CH3:14][OH:15]>CN(C=O)C.C(Cl)(Cl)Cl.[Cu]I>[O:15]1[CH:4]=[CH:2][O:3][CH:14]1[C:6]1[CH:11]=[CH:10][C:9]([N:1]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4](=[O:5])[C:2]2=[O:3])=[CH:8][CH:7]=1

参加物

7

反応物 3

HCID 887MethanolHCID 7054IsatinHCID 24758Sodium hydride

生成物 1

HCID 22016430N-[4-(1,3-dioxolyl)phenyl]isatin

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6212Chloroform溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

Isatin (1.88 g, 0.0128 moles) in anhydrous DMF (100 mL) was cooled in an ice bath under nitrogen and treated with sodium hydride (0.3 g, 1 equivalent). The reaction was warmed to room temperature and stirred for 1 hour. It was then treated with 2-(4-bromophenyl)-1,3-dioxalane (2.83 g, 0.0124 moles) followed by CuI (4.71 g, 2 equivalents). This suspension was heated in an oil-bath at 135° C. under nitrogen for 16 hours. It was then cooled to room temperature and diluted with an equal volume of chloroform. The resulting suspension was filtered and the filtrate was concentrated under reduced pressure. The residue was suspended in xylenes (100 mL) and evaporated to dryness. A thick, viscous oil was recovered which was used as such for the next reaction. TLC (5% methanol in chloroform) showed clean conversion, Rf (product)=0.91.

後処理

  1. temperatureThis suspension was heated in an oil-bath at 135° C. under nitrogen for 16 hours
  2. temperatureIt was then cooled to room temperature
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customevaporated to dryness
  6. customA thick, viscous oil was recovered which
  7. customsuch for the next reaction

出典と根拠

ORDレコード
ord-f6cb9cc586a342d7993bb5fdd588c875
出典データセット
uspto-grants-2009_11
特許番号
US07611909B1

関連ノート

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