反応 #707466

反応方程式

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

triphenylphosphine

3-methoxy-1-butanol

diethyl azodicarboxylate

→

title compound

収率 52.4%

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

収率 52.4%

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
   workup.DISSOLUTIONwas dissolved in methylene chloride
4. 4
   洗浄The solution was washed with 0.4N NaOH, water
5. 5
   その他dried
6. 6
   その他the solvent evaporated
7. 7
   その他The residue was chromatographed over deactivated silica
8. 8
   その他the solvent evaporated
9. 9
   その他The residue (1.7 g) was crystallized from toluene

実験手順

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.

出典