Dimethylcarbamoyl Chloride → 6-Cyano-4,4'-dimethyl-2,2'-bipyridyl

HRID 748281Notes

Reaction equation

HRID 748281 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][N:10]=2)[N+:5]([O-])=[CH:6][CH:7]=1.C[Si]([C:20]#[N:21])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:20]([C:11]1[N:10]=[C:9]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=2)[CH:14]=[C:13]([CH3:15])[CH:12]=1)#[N:21]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 135867924,4'-Dimethyl-2,2'-bipyridyl 1-Oxide

Product 1

HCID 135867966-Cyano-4,4'-dimethyl-2,2'-bipyridylYield 90.3%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

4,4′-Dimethyl-2,2′-bipyridyl N-oxide (3.7 g, 18 mmol) was dissolved in nitroethane (50 ml), and trimethylsilyl cyanide (5.5 g, 55 mmol) and N,N-dimethylcarbamoyl chloride (2.9 g, 27 mmol) were added thereto. The mixture was stirred at room temperature for 36 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (5:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (3.4 g, 87%) as white crystals.

Workup

  1. customThe solvent was evaporated
  2. washThe fractions eluted with hexane-ethyl acetate (5:1
  3. customv/v) were collected
  4. concentrationconcentrated
  5. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-dfb2b4a4354a4bac9741c20e814eaeb2
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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