Water → [2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetonitrile

HRID 890446Notes

Reaction equation

HRID 890446 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:19])=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.[C-:20]#[N:21].[Na+].O>CS(C)=O>[CH3:19][C:4]1[C:3]([CH2:2][C:20]#[N:21])=[CH:8][CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 219357513-Chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 21935781[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetonitrileYield 95.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

27.2 g of 3-chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (95.2 mmol) were dissolved in 100 ml of dimethyl sulfoxide; 5.9 g of sodium cyanide (120 mmol) were added and the mixture was stirred at room temperature for 18 hours. Then, the reaction mixture was poured into a mixture of ice and water and was subsequently extracted with 3 portions of 400 ml of tert-butyl methyl ether. The combined organic phases were washed with water, then with brine and dried with anhydrous sodium sulfate. After evaporation of the solvent, 25.2 g (95.8% of theory) of [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetonitrile were obtained as a pale yellow solid.

Workup

  1. extractionwas subsequently extracted with 3 portions of 400 ml of tert-butyl methyl ether
  2. washThe combined organic phases were washed with water
  3. dry with materialwith brine and dried with anhydrous sodium sulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-a072f5216333442093ece95dfa5917d6
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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