Dimethylcarbamoyl Chloride → [2,2'-Bipyridine]-6-carbonitrile

HRID 748279Notes

Reaction equation

HRID 748279 reaction equation
[N+:1]1([O-])[C:2]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:3][CH:4]=[CH:5][CH:6]=1.C[Si]([C:18]#[N:19])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:18]([C:6]1[N:1]=[C:2]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:3]=[CH:4][CH:5]=1)#[N:19]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 364632,2'-Bipyridine, 1-oxideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 11095236[2,2'-Bipyridine]-6-carbonitrileYield 43%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

2,2′-Bipyridyl N-oxide (2.8 g, 16 mmol) was dissolved in nitroethane (50 ml), and trimethylsilyl cyanide (6.4 g, 65 mmol) and N,N-dimethylcarbamoyl chloride (3.7 g, 35 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 (3:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (1.2 g, 43%) as white crystals.

Workup

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

Sources & evidence

ORD record
ord-0353874786604f389fee54fa8557d362
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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