反応 #707467

反応方程式

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

triphenylphosphine

(±) 1,3 butandiol

diethyl azodicarboxylate

→

title compound

収率 29.3%

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

収率 29.3%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.WAITThe solution was left
2. 2
   その他After evaporation of the solvent the residue
3. 3
   洗浄The solution was washed with 0.4N NaOH, water
4. 4
   その他dried
5. 5
   その他the solvent evaporated
6. 6
   その他The residue was chromatographed over deactivated silica
7. 7
   その他the solvent evaporated
8. 8
   その他The residue was crystallized from methylene chloride-pentane

実験手順

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.

出典