Potassium Carbonate → 6-(2-Picolinyloxy)-2-cyanobenzothiazole

HRID 424454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424454
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[C:10]([C:12]1[S:13][C:14]2[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:15]=2[N:16]=1)#[N:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][O:21][C:19]1[CH:18]=[CH:17][C:15]2[N:16]=[C:12]([C:10]#[N:11])[S:13][C:14]=2[CH:20]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 98819122-Cyano-6-hydroxybenzothiazole

Produkt 1

HCID 584277576-(2-Picolinyloxy)-2-cyanobenzothiazoleAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

(Bromomethyl)pyridine hydrobromide (1.87 g, 7.38 mmol) and 2-cyano-6-hydroxybenzothiazole (1.00 g, 5.68 mmol) were suspended in acetone (50 mL). After introduction of potassium carbonate (1.96 g, 14.2 mmol), the suspension was refluxed for 72 h under nitrogen. After cooling down the mixture and filtering the solids, the filtrate was concentrated and the residue was purified by silica gel chromatography using 50%-75% ethyl acetate in heptane. A yellowish solid was obtained in 72% yield. MS (ESI+): m/z 267.90 (M+H)+; calc'd: 268.05.

Aufarbeitung

  1. temperatureAfter cooling down the mixture
  2. filtrationfiltering the solids
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by silica gel chromatography
  5. customA yellowish solid was obtained in 72% yield

Quellen und Nachweise

ORD-Eintrag
ord-037cc8f24fc549f3a6c5c9059834df06
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106052B2

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