Diethylcarbamoyl chloride → 6-(Propan-2-yl)pyridine-2-carbonitrile

HRID 402174Notes

Reaction equation

HRID 402174 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N+:5]=1[O-])([CH3:3])[CH3:2].[C:11]([Si](C)(C)C)#[N:12].C(N(CC)C(Cl)=O)C.C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=1)#[N:12]

Participants

6

Reactant 4

HCID 6916Diethylcarbamoyl chlorideHCID 11430Potassium CarbonateHCID 82115Trimethylsilyl cyanideHCID 131720791-Oxo-2-(propan-2-yl)-1lambda~5~-pyridine

Product 1

HCID 219927776-(Propan-2-yl)pyridine-2-carbonitrileYield 74.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-isopropylpyridine-N-oxide (104, 1.33 g, 9.7 mmol), cyanotrimethyl-silane (TMS-CN) (1.42 mL, 1.06 g, 11.0 mmol) in 1,2-dichloroethane (40 mL) was stirred at room temperature for 5 min. Then, diethylcarbamoylchloride (Et2NCOCl, 1.23 mL, 9.7 mmol) was added and the mixture was stirred at room temperature under inert atmosphere. After 2 days, a aqueous solution of potassium carbonate (10%) was added and the stirring was continued for 10 min. The organic layer was separated, and the water layer was extracted twice with 1,2-dichloroethane. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1) to give 1.06 g (74%) of the title compound: m/z=147 (M+H)+.

Workup

  1. stirringthe mixture was stirred at room temperature under inert atmosphere
  2. waitAfter 2 days
  3. waitthe stirring was continued for 10 min
  4. customThe organic layer was separated
  5. extractionthe water layer was extracted twice with 1,2-dichloroethane
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1)

Sources & evidence

ORD record
ord-0734f217e242471ea308567471f5e8f4
Source dataset
uspto-grants-2014_06
Patent number
US08741926B2

Reaction notes

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