Reacción #707467

Ecuación de reacción

4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide

triphenylphosphine

(±) 1,3 butandiol

diethyl azodicarboxylate

→

title compound

Rendimiento 29.3%

4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(3-hydroxybut-1-yl)oxybenzamide

Rendimiento 29.3%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITThe solution was left
2. 2
   OtroAfter evaporation of the solvent the residue
3. 3
   LavadoThe solution was washed with 0.4N NaOH, water
4. 4
   Otrodried
5. 5
   Otrothe solvent evaporated
6. 6
   OtroThe residue was chromatographed over deactivated silica
7. 7
   Otrothe solvent evaporated
8. 8
   OtroThe residue was crystallized from methylene chloride-pentane

Procedimiento

A stirred solution of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (2.86 g, 10 mmoles; prepared according to Preparation B), triphenylphosphine (2.62 g, 10 mmoles), (±) 1,3 butandiol (0.90 g, 10 mmoles) in dry tetrahydrofuran (50 ml) was treated dropwise with diethyl azodicarboxylate (1.75 g of 95% purity material, 10 mmoles). The solution was left to stir overnight. After evaporation of the solvent the residue was taken up in methylene chloride. The solution was washed with 0.4N NaOH, water, dried and the solvent evaporated. The residue was chromatographed over deactivated silica using methylene chloride (100), methanol (3), ammonium hydroxide (0.5) solvent system. The appropriate fractions were combined and the solvent evaporated. The residue was crystallized from methylene chloride-pentane to yield 1.05 g (29%) of the title compound. m.p. 136.5°-137.5° C. An additional amount of 0.56 g of material was obtained from the mother liquor after crystallization from toluene, followed by recrystallization from methylene chloride-pentate, and from a dilute solution of ethyl acetate, m.p. 135°-137° C.

Fuente