Dimethylcarbamoyl Chloride → 3-(Cyanomethyl)pyridine-2-carbonitrile

HRID 428551Notes

Reaction equation

HRID 428551 reaction equation
[CH:1]1[CH:6]=[N+:5]([O-])[CH:4]=[C:3]([CH2:8][C:9]#[N:10])[CH:2]=1.C[Si]([C:15]#[N:16])(C)C.CN(C)C(Cl)=O>C(Cl)Cl>[C:9]([CH2:8][C:3]1[C:4]([C:15]#[N:16])=[N:5][CH:6]=[CH:1][CH:2]=1)#[N:10]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 2431673-(Cyanomethyl)pyridin-1-ium-1-olate

Product 1

HCID 46725983-(Cyanomethyl)pyridine-2-carbonitrileYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (1-oxy-pyridin-3-yl)-acetonitrile (10 g, 75 mmol) in anhydrous CH2Cl2 under a nitrogen atmosphere was added trimethylsilylcyanide (10.95 mL, 82 mmol) and dimethylcarbamoylchloride (7.55 mL, 82 mmol). The reaction mixture was stirred at room temperature for 72 hours and then concentrated. EtOAc (100 mL) was added to the residue and the organic phase was washed with 1 M NaOH (150 mL), dried over Na2SO4, filtered and concentrated. The resulting solid was purified by column chromatography (50% EtOAc/hexanes) affording 7.08 g (66%) of a yellow solid: mp 48-51° C.; MS(+)APCI m/z 144 [M+H]+.

Workup

  1. concentrationconcentrated
  2. additionEtOAc (100 mL) was added to the residue
  3. washthe organic phase was washed with 1 M NaOH (150 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid was purified by column chromatography (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c2d975a92a1f4a4eac22a07a0a3142ad
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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