Chlorosuccinimide → 4-acetamido-N-((4-acetylmorpholin-2-yl)methyl)-5-chloro-2-ethoxybenzamide
Reaction equation
[C:1]([NH:4][C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15]([C:19](=[O:21])[CH3:20])[CH2:14]2)=[O:10])=[C:7]([O:24][CH2:25][CH3:26])[CH:6]=1)(=[O:3])[CH3:2].[Cl:27]N1C(=O)CCC1=O>CN(C=O)C>[C:1]([NH:4][C:5]1[C:23]([Cl:27])=[CH:22][C:8]([C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15]([C:19](=[O:21])[CH3:20])[CH2:14]2)=[O:10])=[C:7]([O:24][CH2:25][CH3:26])[CH:6]=1)(=[O:3])[CH3:2]Participants
4
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).