Sodium Cyanide → HCID 66875713, compound

HRID 1479555Notes

Reaction equation

HRID 1479555 reaction equation
[Cl:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][CH:5]=[C:6]([CH2:8]Cl)[CH:7]=1.[C-:12]#[N:13].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][CH:5]=[C:6]([CH2:8][C:12]#[N:13])[CH:7]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 668753003-Chloro-5-(chloromethyl)-2-pyridinecarbonitrile

Product 1

HCID 66875713HCID 66875713, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 3-chloro-5-(chloromethyl)picolinonitrile (from the previous step) in DMSO (0.2 M) was added sodium cyanide (1.25 eq). The reaction mixture was heated at 130° C. under microwave irradiation. The reaction mixture taken up in water and EtOAc, and extracted with EtOAc. Organic phases were dried over anhydrous Na2SO4, and concentrated. Flash chromatography (silica gel, 20-50% EtOAc in hexanes) of the crude afforded 3-chloro-5-(cyanomethyl)picolinonitrile.

Workup

  1. extractionEtOAc, and extracted with EtOAc
  2. dry with materialOrganic phases were dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7ab8705d71ee4d45a88a555305d1b960
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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