Toluene → ethyl 1-benzyl-1H-1,2,3-triazole-4-carboxylate

HRID 1256914

Reaktionsgleichung

Reaktionsgleichung von HRID 1256914
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Br)C1C=CC=CC=1.[N-:16]=[N+:17]=[N-:18].[Na+].[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[CH2:22]>C(O)C.O>[CH2:7]([N:16]1[CH:22]=[C:21]([C:20]([O:24][CH2:25][CH3:26])=[O:23])[N:18]=[N:17]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 7498Benzyl BromideHCID 8821Ethyl AcrylateHCID 33557Sodium Azide

Produkt 1

HCID 849722ethyl 1-benzyl-1H-1,2,3-triazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixed solvent of toluene (100 mL)/ethanol (100 mL)/water (50 mL) were added benzyl bromide (10.7 g) and sodium azide (10.1 g), and the mixture was heated under reflux for 5 hr. A solution of ethyl acrylate (38.8 mL) in ethanol (200 mL) was added dropwise to the reaction mixture, and the mixture was heated under reflux for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (5.66 g) as an oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 12 hr
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-45b169489a484500b043502cdba90eb7
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461209B2

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