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

HRID 1431915

반응식

HRID 1431915 반응식
[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

참가 물질

7

반응물 3

HCID 887MethanolHCID 7054IsatinHCID 24758Sodium hydride

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6212Chloroform용매2회HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f6cb9cc586a342d7993bb5fdd588c875
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07611909B1

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