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

HRID 1531957
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1531957
[C:1](OC)#[N:2].N1C2C(=CC=CC=2)CC1.[C:14]([N:17]1[C:25]2[C:20](=[C:21]([CH3:36])[C:22]([CH2:34]Cl)=[C:23]([CH3:33])[C:24]=2[NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:19][CH2:18]1)(=[O:16])[CH3:15].[C-]#N.[Na+]>CC#N.C1OCCOCCOCCOCCOCCOC1>[C:14]([N:17]1[C:25]2[C:20](=[C:21]([CH3:36])[C:22]([CH2:34][C:1]#[N:2])=[C:23]([CH3:33])[C:24]=2[NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:19][CH2:18]1)(=[O:16])[CH3:15]
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Komponenten

7

Edukt 4

HCID 8929Sodium CyanideHCID 10328Indoline2×HCID 137201Cyanic acid, methyl esterHCID 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-dimethylpropanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2855718-Crown-6Katalysator
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1.27 (9H, S, C(CH3)3), 2.25 (3H, s, -CH3), 2.30 (6H, s, -CH3, >NCOCH3), 3.00 (2H, br, Indoline C3—H), 4.05 (2H, br, Indoline C2—H), 4.68 (2H, s, -CH2c l), 9.16 (1H, br, >NH). (3) N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-propanamide (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-56054b5cf45e428ca0a22880c95415e0
Quelldatensatz
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06200988B1

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