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

HRID 490073Notes

Reaction equation

HRID 490073 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

Reactant 2

HCID 31398ChlorosuccinimideHCID 104738944-acetamido-N-((4-acetylmorpholin-2-yl)methyl)-2-ethoxybenzamide

Product 1

HCID 100463804-acetamido-N-((4-acetylmorpholin-2-yl)methyl)-5-chloro-2-ethoxybenzamideYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure to dryness
  2. customThe residue was triturated with H2O
  3. customthe resulting solids were removed by filtration
  4. customrecrystallized from CH3OH

Sources & evidence

ORD record
ord-a27161bfcc3e41a8b3f81e5b2f27f349
Source dataset
uspto-grants-2009_05
Patent number
US07528131B2

Reaction notes

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