반응 #1173236

반응 방정식

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

triphenylphosphine

3-methoxy-1-butanol

diethyl azodicarboxylate

→

title compound

수율 52.4%

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

수율 52.4%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.WAITThe solution was left
2. 2
   기타After evaporation of the solvent the residue
3. 3
   workup.DISSOLUTIONwas dissolved in methylene chloride
4. 4
   세척The solution was washed with 0.4N NaOH, water
5. 5
   기타dried
6. 6
   기타the solvent evaporated
7. 7
   기타The residue was chromatographed over deactivated silica
8. 8
   기타the solvent evaporated
9. 9
   기타The residue (1.7 g) was crystallized from toluene

실험 절차

A stirred solution of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (1.715 g, 6 mmoles; prepared according to Preparation 1B), triphenylphosphine (1.58 g, 6 mmoles), 3-methoxy-1-butanol (0.62 g, 6 mmoles) in dry tetrahydrofuran (50 ml) was treated dropwise with diethyl azodicarboxylate (1.1 g of 95% purity material, 6 mmoles). The solution was left to stir overnight. After evaporation of the solvent the residue was dissolved 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 (2.5), ammonium hydroxide (0.5) solvent system. The appropriate fractions were combined and the solvent evaporated. The residue (1.7 g) was crystallized from toluene to yield 1.17 g (52%) of the title compound, m.p. 76°-78° C.

출처