Sodium Chloride → [3-Chloro-5-(trifluoromethyl)pyridin-2-yl]acetonitrile

HRID 2100683Notes

Reaction equation

HRID 2100683 reaction equation
[Cl:1][C:2]1[C:3]([CH:12]([C:17]#[N:18])C(OC)=O)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Cl-].[Na+].ClCCl>O.CS(C)=O>[Cl:1][C:2]1[C:3]([CH2:12][C:17]#[N:18])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 6344DichloromethaneHCID 49757460HCID 49757460, compound

Product 1

HCID 16227272[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]acetonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
160 °C

Procedure

314 g (1.13 mol, 1 eq.) of methyl [3-chloro-5-(trifluoromethyl)-2-pyridinyl]-(cyano)acetate and 22 g (0.38 mol, 0.33 eq.) of sodium chloride are dissolved in a solution of 44 mL of water and 1.1 L of dimethyl sulphoxide. The reaction medium is stirred and heated at 160° C. Once all gas has been given off, the medium is cooled to ambient temperature. 1 L of water and 0.5 L of dichloromethane are added. After separation, the aqueous phase is extracted twice with 0.5 L of dichloromethane. The organic phase is washed twice with 0.5 L of water and dried over magnesium sulphate. After concentration, the crude product is diluted in 100 mL of dichloromethane and eluted with an ethyl acetate/heptane mixture (20/80) on a bed of silica. The filtrate is concentrated so as to produce [3-chloro-5-(trifluoromethyl)-2-pyridinyl]acetonitrile.

Workup

  1. temperaturethe medium is cooled to ambient temperature
  2. customAfter separation
  3. extractionthe aqueous phase is extracted twice with 0.5 L of dichloromethane
  4. washThe organic phase is washed twice with 0.5 L of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationAfter concentration
  7. additionthe crude product is diluted in 100 mL of dichloromethane
  8. washeluted with an ethyl acetate/heptane mixture (20/80) on a bed of silica
  9. concentrationThe filtrate is concentrated so as

Sources & evidence

ORD record
ord-bb2033ece0894bc79ffa8328645415da
Source dataset
uspto-grants-2009_08
Patent number
US07572818B2

Reaction notes

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