Diethylcarbamoyl chloride → 5,6-Dimethylpyridine-2-carbonitrile

HRID 1720358Notes

Reaction equation

HRID 1720358 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-].C[Si]([C:14]#[N:15])(C)C.C(N(CC)C(Cl)=O)C>C(Cl)Cl>[CH3:8][C:7]1[CH:6]=[CH:5][C:4]([C:14]#[N:15])=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 82115Trimethylsilyl cyanideHCID 3840573Pyridine, 2,3-dimethyl-, 1-oxide

Product 1

HCID 224176635,6-Dimethylpyridine-2-carbonitrileYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of N-oxide from Step 1 (8.7 g) in CH2Cl2 (125 mL) at r.t. was added trimethylsilylcyanide (9.9 mL, 74.2 mmol). After stirring for 15 minutes, N,N-diethylcarbamoyl chloride (9.4 mL, 74.2 mmol) was added and the resulting mixture was allowed to stir at r.t. for 2.5 days. The reaction was quenched by careful addition of 10% aq. K2CO3, stirred 15 minutes, and extracted (3×) with CH2Cl2. The organic layer was washed with aq. K2CO3, brine, and dried over Na2SO4 /K2CO3. Evaporation of the solvent and purification of the residue by flash chromatography (25% to 50% Et2O in hexanes) yielded 4.13 g of the title compound.

Workup

  1. stirringto stir at r.t. for 2.5 days
  2. customThe reaction was quenched by careful addition of 10% aq. K2CO3
  3. stirringstirred 15 minutes
  4. extractionextracted (3×) with CH2Cl2
  5. washThe organic layer was washed with aq. K2CO3, brine
  6. dry with materialdried over Na2SO4 /K2CO3
  7. customEvaporation of the solvent and purification of the residue by flash chromatography (25% to 50% Et2O in hexanes)

Sources & evidence

ORD record
ord-a37e608360dd488f90aeee738c9177af
Source dataset
uspto-grants-1996_04
Patent number
US05506227

Reaction notes

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