Chlorosuccinimide → N-(4,5-Dichloropyridin-2-yl)pivalamide

HRID 323557Notes

Reaction equation

HRID 323557 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:11]=1>CC#N>[Cl:9][C:10]1[C:15]([Cl:1])=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:21])[CH3:20])[CH:11]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 10656204N-(4-Chloropyridin-2-yl)pivalamide

Product 1

HCID 10538422N-(4,5-Dichloropyridin-2-yl)pivalamideYield 96.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-chloro-succinimide (NCS, 79.45 g, 0.6 mol) was added to a solution of compound 7 (25.8 g, 0.12 mol) in dry CH3CN (300 mL). The resulting suspension was heated at reflux for 2 hours and then cooled to room temperature. After washing with 10% aqueous NaOH (2×150 mL), then water (2×200 mL), the organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a solid. This solid was recrystallized from EtOH to give 28.7 g (95%) of compound 8 as a white solid.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 2 hours
  3. washAfter washing with 10% aqueous NaOH (2×150 mL)
  4. dry with materialwater (2×200 mL), the organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a solid
  8. customThis solid was recrystallized from EtOH

Sources & evidence

ORD record
ord-6b628a8eae9d41bea3d9a99d0250dd96
Source dataset
uspto-grants-2001_04
Patent number
US06214801B1

Reaction notes

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