Reaction #577255

Reaction equation

19

4-acetamido-N-((4-acetylmorpholin-2-yl)methyl)-2-ethoxybenzamide

N-chlorosuccinimide

→

20

Yield 67.4%

4-acetamido-N-((4-acetylmorpholin-2-yl)methyl)-5-chloro-2-ethoxybenzamide

Yield 67.4%

Solvents

DMF

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was then concentrated under reduced pressure to dryness
2. 2
   OtherThe residue was triturated with H2O
3. 3
   Otherthe resulting solids were removed by filtration
4. 4
   Otherrecrystallized from CH3OH

Procedure

A solution of 19 (1.78 g, 4.9 mmol) and N-chlorosuccinimide (0.687 g, 5.1 mmol, 1.05 equiv) in DMF (30 mL) was stirred for 1 h at 70° C. The reaction mixture was then concentrated under reduced pressure to dryness. The residue was triturated with H2O and the resulting solids were removed by filtration and recrystallized from CH3OH to yield 20 (1.314 g).

Source