Reacción #514923

Ecuación de reacción

2-[N-(5-Bromo-2-(2-chloroprop-2-en-1-yloxy)benzyl)-N-ethylamino]-5-cyanopyridine

sodium azide

hydrochloric acid

triethylammonium chloride

→

gum

Rendimiento 104.2%

5-[2-(N-(5-Bromo-2-(2-chloroprop-2-en-1-yloxy)benzyl)-N-ethylamino)-5-pyridyl]-tetrazole

Rendimiento 104.2%

Disolventes

N-methyl pyrrolidone

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate (×2)
2. 2
   Lavadothe combined extracts washed with water (×2)
3. 3
   Secadodried (MgSO4)
4. 4
   Otroevaporated

Procedimiento

2-[N-(5-Bromo-2-(2-chloroprop-2-en-1-yloxy)benzyl)-N-ethylamino]-5-cyanopyridine (reference example 7) (0.40 g, 0.96 mmol), in sieve-dried N-methyl pyrrolidone (10 ml) was treated with sodium azide (189 mg, 12.9 mmol) followed by triethylammonium chloride (208 mg, 1.49 mmol) and the mixture heated at 120° C. (oil bath) for 8 hours. The red solution was taken into ice/water (12 ml), acidified to pH 1-2 with concentrated hydrochloric acid, extracted with ethyl acetate (×2) and the combined extracts washed with water (×2), dried (MgSO4) and evaporated to give a pale red gum (0.45 g). The gum was presorbed to silica (1.2 g) and purified by MPLC to give a colourless title compound as a gum which solidified (135 mg, 31%).

Fuente