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

HRID 384675Notes

Reaction equation

HRID 384675 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.[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>C(#N)C>[Cl:9][C:10]1[C:15]([Cl:8])=[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 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NCS (3.14 g. 23.5 mmol) was added to a solution of N-(4-chloropyridin-2-yl)pivalamide (1.00 g, 4.7 mmol) in dry acetonitrile (10 mL). The resulting suspension was heated for 3 h and then cooled to r.t. The solvent was removed in vacuo and the crude mixture was diluted with ethyl acetate (50 mL). The organic phase was washed with aqueous NaOH (10%, 2×20 mL), water (20 mL) and dried (MgSO4). The solvent was removed in vacuo and the crude mixture was purified by flash chromatography on silica, eluting with ethyl acetate and hexane (1/9), to give the title compound as a colourless solid (0.87 g, 75%).

Workup

  1. temperatureThe resulting suspension was heated for 3 h
  2. customThe solvent was removed in vacuo
  3. additionthe crude mixture was diluted with ethyl acetate (50 mL)
  4. washThe organic phase was washed with aqueous NaOH (10%, 2×20 mL), water (20 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe crude mixture was purified by flash chromatography on silica
  8. washeluting with ethyl acetate and hexane (1/9)

Sources & evidence

ORD record
ord-695609b69ed944b090847712fcf74d93
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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