Phenylacetonitrile → 2-Phenyl-2-[4-(4-pyridyl)-2-thiazolyl]acetonitrile

HRID 2309800

Reaktionsgleichung

Reaktionsgleichung von HRID 2309800
Cl[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[N:6]=1.[CH2:13]([C:20]#[N:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2-].[Na+]>C1(C)C=CC=CC=1>[C:14]1([CH:13]([C:2]2[S:3][CH:4]=[C:5]([C:7]3[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=3)[N:6]=2)[C:20]#[N:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 8794PhenylacetonitrileHCID 24533Sodium amideHCID 140969694-(2-chloro-4-thiazolyl)Pyridine

Produkt 1

HCID 140969702-Phenyl-2-[4-(4-pyridyl)-2-thiazolyl]acetonitrileAusbeute 8,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-chloro-4-(4-pyridyl)thiazole (1.00 g, 0.005 mol) and benzylcyanide (1.18 g, 0.010 mol) in dry toluene (10 mL) at 5° C. was added sodamide (400 mg, 0.010 mol) and the mixture heated to 100° C. for 20 minutes. After cooling, the mixture was quenched with water, the layers separated, and the aqueous phase washed with methylene chloride (2×50 mL). The combined extracts were dried over sodium sulfate, concentrated, and chromatographed through silica gel (3:1 ethyl acetate/methylene chloride as eluant). After decolorizing with charcoal, recrystallization from hexane/ethyl acetate afforded 2-phenyl-2-[4-(4-pyridyl)-2-thiazolyl]acetonitrile (115 mg, 8%). mp. 110°-111° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe mixture was quenched with water
  3. customthe layers separated
  4. washthe aqueous phase washed with methylene chloride (2×50 mL)
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. concentrationconcentrated
  7. customchromatographed through silica gel (3:1 ethyl acetate/methylene chloride as eluant)
  8. customAfter decolorizing with charcoal, recrystallization from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2b1883d8b1254a13a2b18e91b8b52e3b
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04697012

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