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Sodium Cyanide → N-(1-acetyl-5-cyanomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

HRID 1107947
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1107947
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:23])[C:9]([CH2:21]Cl)=[C:10]([CH3:20])[C:11]=2[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C-:24]#[N:25].[Na+]>CC#N.C1OCCOCCOCCOCCOCCOC1>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:23])[C:9]([CH2:21][C:24]#[N:25])=[C:10]([CH3:20])[C:11]=2[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]
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Komponenten

5

Edukt 2

HCID 8929Sodium CyanideHCID 15895572N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

Produkt 1

HCID 15524343N-(1-acetyl-5-cyanomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamideAusbeute 75,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2855718-Crown-6KatalysatorHCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide (21 g) was suspended in CH3CN (150 ml), and NaCN (8.1 g) and 18-crown-6 (870 mg) were added, which was followed by refluxing for 15 hr. CH3CN was evaporated under reduced pressure and CHCl3 (300 ml) was added. The mixture was washed with water and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The obtained residue was washed with boiling MeOH to give 15.5 g of N-(1-acetyl-5-cyanomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide.

Aufarbeitung

  1. temperatureby refluxing for 15 hr
  2. customCH3CN was evaporated under reduced pressure and CHCl3 (300 ml)
  3. additionwas added
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customCHCl3 was evaporated under reduced pressure
  7. washThe obtained residue was washed with boiling MeOH

Quellen und Nachweise

ORD-Eintrag
ord-2c019cbe049342cea065ce9e94e03949
Quelldatensatz
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06063806

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