N-[(2,4-dichloro-1,3-thiazol-5-yl)methylidene]hydroxylamine → 2,4-Dichloro-5-cyanothiazole

HRID 1584026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1584026
[Cl:1][C:2]1[S:3][C:4]([CH:8]=[N:9]O)=[C:5]([Cl:7])[N:6]=1>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[S:3][C:4]([C:8]#[N:9])=[C:5]([Cl:7])[N:6]=1

Komponenten

3

Edukt 1

HCID 2778786N-[(2,4-dichloro-1,3-thiazol-5-yl)methylidene]hydroxylamine

Produkt 1

HCID 155763592,4-Dichloro-5-cyanothiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
137 °C

Versuchsvorschrift

400 g (2.03 mol) of crude 2,4,-dichloro-5-thiazolecarboxaldehyde oxime (IV) are stirred with 2 liters of acetic anhydride at reflux temperature (137° C.) for 4 hours. Fractionation using a silvered distillation column 1 m long provided 271 g (=75.7% of theory) of 2,4-dichloro-5-thiazolecarbonitrile (V) at 112° C./20 m bar, this product being identical by mass and IR spectroscopy with that described in German Offenlegungsschrift No. 3,038,608 (which can also be named 2,4-dichloro-5-cyanothiazole). The compound solidifies at room temperature to give colourless crystals which can be recrystallized from petroleum ether. Melting point: 34°-35° C.

Aufarbeitung

  1. distillationa silvered distillation column 1 m long provided 271 g (=75.7% of theory) of 2,4-dichloro-5-thiazolecarbonitrile (V) at 112° C./20 m bar
  2. customsolidifies at room temperature
  3. customto give colourless crystals which
  4. customcan be recrystallized from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-181ad24b7c3042988f674c4f253ff3c3
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04555577

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