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

HRID 1471276

Reaction equation

HRID 1471276 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-571b693cc1d94eee9f29a08dd293f5e3
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Linked notes

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