반응 #707467

반응 방정식

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

triphenylphosphine

(±) 1,3 butandiol

diethyl azodicarboxylate

→

title compound

수율 29.3%

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

수율 29.3%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.WAITThe solution was left
2. 2
   기타After evaporation of the solvent the residue
3. 3
   세척The solution was washed with 0.4N NaOH, water
4. 4
   기타dried
5. 5
   기타the solvent evaporated
6. 6
   기타The residue was chromatographed over deactivated silica
7. 7
   기타the solvent evaporated
8. 8
   기타The residue was crystallized from methylene chloride-pentane

실험 절차

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.

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