Acetonitrile → Sodium 2-cyano-1-(1,3-thiazol-5-yl)ethenolate

HRID 1055690

Reaktionsgleichung

Reaktionsgleichung von HRID 1055690
[S:1]1[C:5]([C:6]([O:8]C)=O)=[CH:4][N:3]=[CH:2]1.[C:10](#[N:12])[CH3:11].[H-].[Na+:14].C(OC)(C)(C)C>C1COCC1>[C:10]([CH:11]=[C:6]([C:5]1[S:1][CH:2]=[N:3][CH:4]=1)[O-:8])#[N:12].[Na+:14]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 331117Methyl 1,3-thiazole-5-carboxylate2×

Produkt 1

HCID 86690968Sodium 2-cyano-1-(1,3-thiazol-5-yl)ethenolate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 1.5 g (10.5 mmol) of methyl 1,3-thiazole-5-carboxylate and 430 mg (10.8 mmol) of acetonitrile in 15 ml of THF was added dropwise to a suspension of 419 mg of sodium hydride (60% strength suspension in mineral oil) in 16 ml of THF which was heated under reflux. The reaction mixture was heated under reflux for 20 h. After cooling, 50 ml of methyl tert-butyl ether were added and the mixture was stirred for 30 minutes. The resulting precipitate was filtered off with suction through a frit and dried under oil pump vacuum. This gave 1.71 g (94% of theory) of the title compound which was combined with the product (3.48 g, 95% of theory) from a second batch starting with 3.0 g (21 mmol) of methyl 1,3-thiazole-5-carboxylate. This material was used without further characterization for the next step.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 20 h
  5. temperatureAfter cooling
  6. filtrationThe resulting precipitate was filtered off with suction through a frit
  7. customdried under oil pump vacuum

Quellen und Nachweise

ORD-Eintrag
ord-afcb85efea60443db2e684e976808815
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394309B2

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