Water → N-(6-Chloropyridin-2-yl)-2,2-dimethylpropanamide

HRID 1750069Notes

Reaction equation

HRID 1750069 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:8][C:9]1[N:14]=[C:13]([NH2:15])[CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.O>C(Cl)Cl>[Cl:8][C:9]1[N:14]=[C:13]([NH:15][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 2062462-Amino-6-chloropyridine

Product 1

HCID 13154248N-(6-Chloropyridin-2-yl)-2,2-dimethylpropanamideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pivaloyl chloride (18.7 mL, 151.6 mmol) was slowly added to an ice-cooled solution of 6-chloropyridin-2-amine (15 g, 116.7 mmol) and triethylamine (24.25 mL, 124.96 mmol) in DCM (180 mL). The mixture was stirred in an ice-bath for 15 min and then at rt for 6 h. The mixture was poured into water. The organic layer was washed with saturated aq NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give N-(6-chloropyridin-2-yl)pivalamide (intermediate 5) (20.01 g, 81%) as a yellow solid.

Workup

  1. waitat rt for 6 h
  2. washThe organic layer was washed with saturated aq NaHCO3, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b5b8afc7ec04369881912613fb7c6f8
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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