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

HRID 530806Notes

Reaction equation

HRID 530806 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-].[Si]([C:14]#[N:15])(C)(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-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 2 in Scheme 4-3 (98 mg, 0.8 mmol) in DCM (10 mL) was added TMSCN (0.2 mL) at room temperature. After the mixture was stirred for 30 min, diethylcarbamic chloride (0.2 mL) was added, and stirred for 24 h. The mixture was concentrated and the residue was purified by combi-flash (MeOH/H2O (NH4HCO3)) to give a white solid. LCMS (ESI) m/z=134 (M+H)+.

Workup

  1. stirringstirred for 24 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by combi-flash (MeOH/H2O (NH4HCO3))
  4. customto give a white solid

Sources & evidence

ORD record
ord-7ab4cc325e824fa5bc482a4037503fab
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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