N-bromobutanimide → N-(5-bromo-4-chloropyridin-2-yl)-2,2-dimethylpropanamide

HRID 384679Notes

Reaction equation

HRID 384679 reaction equation
C1C(=O)N([Br: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>[Br:8][C:15]1[C:10]([Cl:9])=[CH:11][C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:21])[CH3:20])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 10656204N-(4-Chloropyridin-2-yl)pivalamide

Product 1

HCID 59613421N-(5-bromo-4-chloropyridin-2-yl)-2,2-dimethylpropanamideYield 66.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NBS (8.37 g. 47.0 mmol) was added to a solution of N-(4-chloropyridin-2-yl)pivalamide (2.00 g, 9.40 mmol) in dry acetonitrile (20 mL). The resulting suspension was heated for 3 hr and then cooled to r.t. The solvent was removed in vacuo and the crude mixture was diluted with ethyl acetate (100 mL). The organic phase was washed with aqueous NaOH (10%, 2×40 mL), water (40 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 (1.82 g, 66%).

Workup

  1. temperatureThe resulting suspension was heated for 3 hr
  2. customThe solvent was removed in vacuo
  3. additionthe crude mixture was diluted with ethyl acetate (100 mL)
  4. washThe organic phase was washed with aqueous NaOH (10%, 2×40 mL), water (40 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-a0fce03ae79e4e8882d8fa7ee697e6d1
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

Loading…