Dimethylcarbamoyl Chloride → 6-(1,3-Oxazol-5-yl)-2-pyridinecarbonitrile

HRID 748272Notes

Reaction equation

HRID 748272 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N+:7]=2[O-])=[CH:4][N:3]=[CH:2]1.C[Si]([C:17]#[N:18])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[O:1]1[C:5]([C:6]2[N:7]=[C:8]([C:17]#[N:18])[CH:9]=[CH:10][CH:11]=2)=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 59750255HCID 59750255, compound

Product 1

HCID 229395296-(1,3-Oxazol-5-yl)-2-pyridinecarbonitrileYield 75%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

2-(1,3-Oxazol-5-yl)pyridine N-oxide (1.0 g, 6.6 mmol) was dissolved in nitroethane (15 ml), and trimethylsilyl cyanide (2.7 g, 27.2 mmol) and N,N-dimethylcarbamoyl chloride (3.0 g, 27.8 mmol) were added thereto. The mixture was stirred at room temperature for 5 days. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (1:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (0.84 g, 75%).

Workup

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

Sources & evidence

ORD record
ord-84522536d45a47cd81fc064dc98a4b96
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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