Formamide → 1-(2-Bromophenyl)-1H-1,2,4-triazole

HRID 478250

Reaktionsgleichung

Reaktionsgleichung von HRID 478250
Cl.[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].Cl[CH2:12]Cl.[CH:14]([NH2:16])=O>>[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:14]=[N:16][CH:12]=[N:10]1

Komponenten

4

Edukt 3

HCID 713FormamideHCID 6344DichloromethaneHCID 27239122-Bromophenylhydrazine hydrochloride

Produkt 1

HCID 180012721-(2-Bromophenyl)-1H-1,2,4-triazole

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A suspension of 2-bromophenylhydrazine hydrochloride (5.0 g, 22 mmol) in formamide (10 ml) was heated at 140° C. for 16 h. The reaction mixture was cooled to ambient temperature, diluted into dichloromethane (50 ml) and washed with water (3×20 ml). The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. Purification by chromatography on silica gel eluting with dichloromethane gave 1-(2-bromophenyl)-1H-[1,2,4]triazole (4.80 g) as a tan solid: δH (400 MHz, CDCl3) 8.49 (1H, s), 8.14 (1H, s), 7.76 (1H, dd, J 1 and 8), 7.44-7.53 (2H, m), 7.34-7.39 (1H, m).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washwashed with water (3×20 ml)
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification by chromatography on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-67e18148d26a47ecb1294ca13ced64a0
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642229B2

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