Triethylamine → 2-(Pivaloylamino)pyridine

HRID 1699228Notes

Reaction equation

HRID 1699228 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:15](Cl)(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]>ClCCl>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 62493Pivaloyl chloride

Product 1

HCID 10515192-(Pivaloylamino)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 94.1 g (1.0 mol) of 2-aminopyridine and 173 ml (1.25 mol) of triethylamine in 400 ml of dichloromethane were added dropwise, whilst cooling with ice water, 132.5 g (1.099 mol) of pivaloyl chloride in 150 ml of dichloromethane. The mixture was stirred for 2 hours at room temperature and filtered to remove the triethylamine hydrochloride formed. The filtrate was washed with water and twice with 5% aqueous sodium hydrogen carbonate solution, then dried over sodium sulphate. After working up in the usual way 157.5 g (88.4% of theory) of colourless crystals of melting point 74-76° C. were obtained.

Workup

  1. filtrationfiltered
  2. customto remove the triethylamine hydrochloride
  3. customformed
  4. washThe filtrate was washed with water and twice with 5% aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over sodium sulphate
  6. customwere obtained

Sources & evidence

ORD record
ord-d886a7be82fa4e2293be29ba15bb20f6
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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