Reaktion #1173236

Reaktionsgleichung

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

triphenylphosphine

3-methoxy-1-butanol

diethyl azodicarboxylate

→

title compound

Ausbeute 52.4%

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

Ausbeute 52.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle