Sodium Hydroxide → 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile

HRID 2120711

Reaktionsgleichung

Reaktionsgleichung von HRID 2120711
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[C:24](#[N:32])[C:25]1[C:26](=[CH:28][CH:29]=[CH:30][CH:31]=1)[NH2:27].[OH-].[Na+]>O1CCCC1.C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[N:27][C:26]1[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=1[C:24]#[N:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 24813Phosphorus oxychlorideHCID 729132-AminobenzonitrileHCID 791761-Benzyl-3-pyrrolidone

Produkt 1

HCID 7584062-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrileAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The compound 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile (Compound 24) was synthesized by mixing chloroform (25 mL), tetrahydrofuran (25 mL), 1-benzyl-2-pyrrolidinone (5.16 g, 29.4 mmol), phosphorus oxychloride (5.2 mL) and tin(IV) chloride (1.0 mL), stirring at room temperature for 1.5 hours, and adding anthranilonitrile (3.3 g, 27.9 mmol) in portions. The mixture was then stirred at 50° C. for 5 hours under heating and ice-water (15 mL) and 10% aqueous sodium hydroxide solution was added to make weak alkaline. The organic solvent was removed under reduced pressure and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and condensed under vacuum. The crude product was purified by flash chromatography (chloroform-methanol, 100:1) to yield 7.0 g (91%) Compound 24 as slightly yellow needles; mp 59-61° C.; IR (KBr): 2217, 1628, 1439, 1279 cm−1; 1H NMR (DMSO-d6): δ 7.06-7.69 (m, 9H), 4.83 (s, 2H), 3.46 (t, 2H), 2.60 (t, 2H), 2.10 (m, 2H); 13C NMR (CDCl3): δ 162.8, 156.3, 137.6, 133.7, 132.9, 128.7, 128.3, 127.4, 122.8, 121.7, 118.8, 105.9, 48.3, 47.3, 27.7, 19.6. Anal. Calcd. for C18H17N3(275.35): C, 78.52; H, 6.22; N, 15.26. Found: C, 78.37; H, 6.20; N, 15.17.

Aufarbeitung

  1. customThe compound 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile (Compound 24) was synthesized
  2. stirringThe mixture was then stirred at 50° C. for 5 hours
  3. temperatureunder heating
  4. customThe organic solvent was removed under reduced pressure
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialThe extract was dried over anhydrous sodium sulfate and condensed under vacuum
  7. customThe crude product was purified by flash chromatography (chloroform-methanol, 100:1)

Quellen und Nachweise

ORD-Eintrag
ord-0edaa50437ac404e812d62f234153de7
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693112B2

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