Triethylamine → HCID 3614744, compound

HRID 984133Notes

Reaction equation

HRID 984133 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](C)([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])[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 62493Pivaloyl chloride

Product 1

HCID 3614744HCID 3614744, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EX-5A) A solution of 2-amino pyridine (20.42 , 217.0 mmol) in dichloromethane 500 mL was cooled to 0° C. and treated with triethyl amine (36.29 mL, 260.4 mmol) and pivaloyl chloride (28.06 mL, 227.8 mmol). After 15 minutes, the reaction mixture was allowed to warm to room temperature and stir overnight. The reaction mixture was poured onto ice, and the organic layer was washed with saturated NaHCO3 (aq), and dried over Na2SO4. The volatile components were removed, and a brown oil was isolated. Crystallization with hexanes afforded 31 g of N-(pyrid-2-yl)-2,2-dimethylacetamide (EX-5A) as white crystals in 80% yield. Reference: Turner, J. A. J. Org. Chem, 1983, 48, 3401.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. washthe organic layer was washed with saturated NaHCO3 (aq)
  3. dry with materialdried over Na2SO4
  4. customThe volatile components were removed
  5. customa brown oil was isolated
  6. customCrystallization with hexanes

Sources & evidence

ORD record
ord-d632806017f748468da87d9ef74ae0c1
Source dataset
uspto-grants-2005_03
Patent number
US06867217B1

Reaction notes

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