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

HRID 6603

반응식

HRID 6603 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+].Br[C:15]1[CH:16]=[C:17]([CH:21]2[O:25][CH2:24][CH2:23][O:22]2)[CH:18]=[CH:19][CH:20]=1.CO>CN(C=O)C.C(Cl)(Cl)Cl.[Cu]I>[O:22]1[CH:23]=[CH:24][O:25][CH:21]1[C:17]1[CH:16]=[C:15]([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:20]=[CH:19][CH:18]=1

참가 물질

8

반응물 4

HCID 887MethanolHCID 7054IsatinHCID 24758Sodium hydrideHCID 873062-(3-Bromophenyl)-1,3-dioxolane

생성물 1

HCID 21972258N-[3-(1,3-dioxolyl)phenyl]isatin

시약·촉매·용매 3

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

반응 조건

온도
0 °C

실험 절차

Isatin (3.2 g, 0.0218 mol) was dissolved in anhydrous DMF (75 mL) and cooled in an ice-bath under a nitrogen atmosphere. To this cold solution, sodium hydride (0.575 g, 0.0239 mol) was added and the reaction was stirred at 0° C. for 1.5 hours. This solution was then treated with 2-(3-bromophenyl)-1,3-dioxolane (5 g, 1 equivalent) followed by CuI (8.3 g, 2 equivalents). The resulting suspension was heated in an oil-bath under nitrogen at 130–140° C. for 16 hours. It was then cooled to room temperature and diluted with an equal volume of chloroform. This suspension was filtered and the filtrate was concentrated under reduced pressure. A viscous brown oil was recovered which was suspended in xylenes (150 mL) wand evaporated to dryness. The residue was used as such for the next reaction. TLC (5% methanol in chloroform) showed clean conversion; Rf (product)=0.86.

후처리

  1. temperaturecooled in an ice-bath under a nitrogen atmosphere
  2. temperatureThe resulting suspension was heated in an oil-bath under nitrogen at 130–140° C. for 16 hours
  3. temperatureIt was then cooled to room temperature
  4. filtrationThis suspension was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customA viscous brown oil was recovered which
  7. customwand evaporated to dryness
  8. customsuch for the next reaction

출처 및 근거

ORD 기록
ord-4307fdaae0dc4d9bb621a9607ef82b36
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07083986B2

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