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

HRID 861977Notes

Reaction equation

HRID 861977 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]>C(Cl)Cl>[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 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 3-L flask equipped with a nitrogen (N2) inlet, thermometer and addition funnel was charged with dichloromethane (CH2Cl2, 1400 mL) and 2-amino-6-methylpyridine (130 g, 1.2 mol, Aldrich). After cooling the reaction to 0° C. in a wet ice/water bath, triethylamine (Et3N, 151.5 g, 1.5 mol) was added. Trimethylacetyl chloride (159.15 g, 1.32 mol) was diluted with CH2Cl2 (100 mL) and added dropwise to the reaction over 1.5 h. The reaction was stirred for an additional 30 min at room temperature. The salts were filtered from the reaction and the filtrate was washed twice with H2O. Drying the filtrate with anhydrous magnesium sulfate (MgSO4) and stripping all solvent in vacuo left a yellowish colored solid. Recrystallization from diethyl ether (Et2O)/hexanes (Hex) provided 167.3 g (73%) of pure product. The identity of this material and that of subsequent examples were confirmed by NMR (300 MHZ), microanalysis, and infrared spectroscopy, unless otherwise noted.

Workup

  1. customA 3-L flask equipped with a nitrogen (N2) inlet
  2. additionthermometer and addition funnel
  3. temperatureAfter cooling
  4. customthe reaction to 0° C. in a wet ice/water bath
  5. additionadded dropwise to the reaction over 1.5 h
  6. filtrationThe salts were filtered from the reaction
  7. washthe filtrate was washed twice with H2O
  8. dry with materialDrying the filtrate with anhydrous magnesium sulfate (MgSO4)
  9. waitleft a yellowish colored solid
  10. customRecrystallization from diethyl ether (Et2O)/hexanes (Hex)

Sources & evidence

ORD record
ord-4c747d3bc0e741a18a448b33a9ab2c48
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

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