Ethyl Acetate → 4-(2-Azidomethyl-phenyl)-[1,2,3]thiadiazole

HRID 397497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397497
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[N:11][S:12][CH:13]=1.[N-:14]=[N+:15]=[N-:16].[Na+].C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C>CN(C)C=O>[N:14]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[N:11][S:12][CH:13]=1)=[N+:15]=[N-:16]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 21226206Ethyl acetate hexaneHCID 218662434-(2-Bromomethyl-phenyl)-[1,2,3]thiadiazole

Produkt 1

HCID 218662814-(2-Azidomethyl-phenyl)-[1,2,3]thiadiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(2-bromomethyl-phenyl)-[1,2,3]thiadiazole (7.0 g, 0.027 mol) and sodium azide (5.3 g, 0.081 mol) in N,N-dimethylformamide (200 ml) was stirred at room temperature overnight. Ethyl acetate was added and the reaction mixture was washed with water and brine. Drying and solvent evaporation gave an oil; flash chromatography (silica gel, hexane-ethyl acetate, 96:4) gave 4-(2-azidomethyl-phenyl)-[1,2,3]thiadiazole; 1H NMR (CDCl3, 300 MHz) δ8.74 (s, 1H), 7.76 (m, 1H), 7.53 (m, 3H), 4.54 (s, 2H).

Aufarbeitung

  1. washthe reaction mixture was washed with water and brine
  2. customDrying
  3. customsolvent evaporation
  4. customgave an oil

Quellen und Nachweise

ORD-Eintrag
ord-037756aa0ef6463a8baae3eda02eb1ad
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610701B2

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