Reacción #732836

Ecuación de reacción

sodium azide

triethylamine

2,3 dichlorophenylisocyanate

cyclohexylmethylamine

→

title compound

Rendimiento 56.3%

N-(cyclohexylmethyl)-1-(2,3-dichlorophenyl)-1H-tetrazol-5-amine

Rendimiento 56.3%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   Filtraciónwas filtered through Celite
3. 3
   Concentraciónthe organics concentrated in vacuo
4. 4
   OtroThe crude residue was purified by column chromatography (gradient elution; 25% ethyl acetate/hexanes to 35%)

Procedimiento

To a solution of 2,3 dichlorophenylisocyanate (0.1 g, 0.49 mmol) in 5 mL anhydrous tetrahydrofuran was added cyclohexylmethylamine (0.1 g). The solution was stirred at room temperature for 2 h when mercury (II) acetate (0.13 g, 0.49 mmol), sodium azide (0.095 g, 1.47 mmol) and triethylamine (0.148 g, 1.47 mmol) were added. The resulting suspension was stirred at room temperature for 12 hours, at which time the precipitate was filtered through Celite and the organics concentrated in vacuo. The crude residue was purified by column chromatography (gradient elution; 25% ethyl acetate/hexanes to 35%) to give 0.09 g of the title compound as a sticky foam. MS (ESI/NH3) m/z 325 (M+H)+ 1H NMR (δ, DMSO-d6) 0.8-0.95 (m, 2H), 1.05-1.3 (m, 3H), 1.5-1.8 (m, 7H), 3.05-3.12 (t, 2H), 7.05-7.17 (t, 1H), 7.58-7.65 (m, 2H), 7.90-7.95 (d, 1H).

Fuente