Triethylamine → N-(6-Methylpyridin-2-yl)pivalamide

HRID 656292Notes

Reaction equation

HRID 656292 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C(N(CC)CC)C.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19]>ClCCl>[CH3:16][C:17]([CH3:22])([CH3:21])[C:18]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1)=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 157652-Amino-6-methylpyridineHCID 62493Pivaloyl chloride

Product 1

HCID 3251458N-(6-Methylpyridin-2-yl)pivalamideYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-amino-6-picoline (26 g) was dissolved in dichloromethane (280 ml) and the reactor was cooled to 0° C., followed by adding triethylamine (30 g) thereto. To the obtained solution was slowly added dropwise a solution of trimethylacetylchloride (31.8 g) in dichloromethane (20 ml) and the mixture was stirred at room temperature for 3 hours. The resulting mixture was filtered, washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and then crystallized (dichloromethane/petroleum ether) to yield a pale yellow solid (38 g, 82%).

Workup

  1. filtrationThe resulting mixture was filtered
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customcrystallized (dichloromethane/petroleum ether)

Sources & evidence

ORD record
ord-4426d1f5d4a0452eb78109d2e8e31bb3
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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