4-Chlorobenzonitrile → HCID 57750306, Verbindung

HRID 423105

Reaktionsgleichung

Reaktionsgleichung von HRID 423105
[Li+].CCC[CH2-].[CH3:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1>C1COCC1>[Cl:12][C:13]1[CH:20]=[CH:19][C:16](/[C:17](/[NH2:18])=[CH:6]/[C:7]2[S:8][CH:9]=[CH:10][N:11]=2)=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 121634-ChlorobenzonitrileHCID 61028n-Butyl lithiumHCID 771292-Methylthiazole

Produkt 1

HCID 57750306HCID 57750306, VerbindungAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

A 2.5M solution of N-butyllithium (8.00 mL, 20.00 mmol) in hexanes, was added dropwise to 2-methylthiazole (1.983 g, 20 mmol) dissolved in THF (35.00 mL) over a period of 5 minutes under argon at −70° C. The resulting pale yellow slurry was stirred at −70° C. for 2.5 hour. 4-chlorobenzonitrile (2.75 g, 20.00 mmol) in THF (35.00 mL) was added dropwise to the suspension, which was stirred at −70° C. for 90 minutes after the end of the addition. The reaction mixture was allowed to warm to room temperature under stirring and darkened. The crude was concentrated to dryness and diluted with ethyl acetate then washed with water, dried over magnesium sulphate and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 10 to 100% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford (Z)-1-(4-chlorophenyl)-2-(thiazol-2-yl)ethenamine (1.466 g, 31.0%) as a pale yellow solid.

Aufarbeitung

  1. stirringwas stirred at −70° C. for 90 minutes
  2. additionafter the end of the addition
  3. temperatureto warm to room temperature
  4. stirringunder stirring
  5. concentrationThe crude was concentrated to dryness
  6. additiondiluted with ethyl acetate
  7. washthen washed with water
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography on silica gel eluting with 10 to 100% ethyl acetate in dichloromethane
  11. customThe solvent was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-39b6bfe9ef8a414ea5978e6c0eb883e2
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101623B2

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