Dimethyl Sulfoxide → 2-(6-Methylpyridin-3-yl)acetonitrile

HRID 717748Notes

Reaction equation

HRID 717748 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[N:10][CH:11]=1.CS(C)=O.CCOC(C)=O>O>[CH3:12][C:9]1[N:10]=[CH:11][C:6]([CH2:5][C:1]#[N:2])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 122143385-(Chloromethyl)-2-methylpyridine

Product 1

HCID 114577152-(6-Methylpyridin-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

Sodium cyanide (38.6 g, 787.7 mmol, 1.5 equiv), 5-(chloromethyl)-2-methylpyridine (74.37 g, 527.4 mmol, 1 equiv) and DMSO (750 mL, 10 vol) were charged into a reactor and placed under nitrogen. This exothermic mixture self-heated to ca. 45° C. and was heated to 60° C. After 15 min, TLC (eluent: EtOAc:heptanes 50/50) indicated that the reaction was completed. The mixture was cooled to RT and water (1500 mL, 20 vol) was added slowly; the exotherm was controlled by the addition rate. The solution was extracted with EtOAc (4×750 mL), and the combined organic layer was concentrated under reduced pressure. The resulting oil was purified by chromatography (eluent: EtOAc), to obtain 2-(6-methylpyridin-3-yl)acetonitrile.

Workup

  1. temperaturewas heated to 60° C
  2. temperatureThe mixture was cooled to RT
  3. extractionThe solution was extracted with EtOAc (4×750 mL)
  4. concentrationthe combined organic layer was concentrated under reduced pressure
  5. customThe resulting oil was purified by chromatography (eluent: EtOAc)

Sources & evidence

ORD record
ord-8f0b3566e9524c7a89f383d111a9c654
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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