Reaktion #707467

Reaktionsgleichung

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

triphenylphosphine

(±) 1,3 butandiol

diethyl azodicarboxylate

→

title compound

Ausbeute 29.3%

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

Ausbeute 29.3%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe solution was left
2. 2
   SonstigeAfter evaporation of the solvent the residue
3. 3
   WaschenThe solution was washed with 0.4N NaOH, water
4. 4
   Sonstigedried
5. 5
   Sonstigethe solvent evaporated
6. 6
   SonstigeThe residue was chromatographed over deactivated silica
7. 7
   Sonstigethe solvent evaporated
8. 8
   SonstigeThe residue was crystallized from methylene chloride-pentane

Vorschrift

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.

Quelle