Acetonitrile → 2,2-dimethyl-N,N-dipyridin-2-ylpropanamide

HRID 1926528

Reaction equation

HRID 1926528 reaction equation
[CH:1]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]=[CH:3][CH:2]=1.C(#N)C.C(N(CC)CC)C.[CH3:24][C:25]([CH3:30])([CH3:29])[C:26](Cl)=[O:27]>O>[CH3:24][C:25]([CH3:30])([CH3:29])[C:26]([N:7]([C:5]1[CH:6]=[CH:1][CH:2]=[CH:3][N:4]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][N:13]=1)=[O:27]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 145472,2'-DipyridylamineHCID 62493Pivaloyl chloride

Product 1

HCID 666280902,2-dimethyl-N,N-dipyridin-2-ylpropanamideYield 60.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask were added 2.0 g of 2,2′-dipyridylamine and 35 ml of acetonitrile. The solution was stirred under nitrogen and cooled to 5 C, when 1.5 g of triethylamine were added, followed by 1.5 g of trimethylacetyl chloride and the mixture was allowed to warm to 22 C. After 1 hour, 50 ml of water were added and the acetonitrile was removed. The product was extracted with ethyl acetate and washed with water. Following solvent removal, the product was purified by silica gel chromatography using 50% ethyl acetate in hexane, resulting in 1.8 g of an oil that solidified on standing.

Workup

  1. additionwere added
  2. temperatureto warm to 22 C
  3. customthe acetonitrile was removed
  4. extractionThe product was extracted with ethyl acetate
  5. washwashed with water
  6. customFollowing solvent removal
  7. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-312a789c007b4315aa3e685d43a52a09
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Linked notes

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