Sodium Azide → HCID 22615270, compound

HRID 842709Notes

Reaction equation

HRID 842709 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[C:4]([CH2:10]Cl)[N:3]=1.[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[N:12]([CH2:10][C:4]1[N:3]=[C:2]([Cl:1])[C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 226152712-Chloro-6-(chloromethyl)nicotinonitrile

Product 1

HCID 22615270HCID 22615270, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-chloro-6-chloromethyl-3-cyanopyridine (600 mg, 3.21 mmol) and sodium azide (229 mg, 3.53 mmol) in DMF (12 mL) were stirred at 50° C. for 30 min. The mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with water (2 times) and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography on silica (chloroform) to give the title compound as an oil:

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with water (2 times) and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica (chloroform)

Sources & evidence

ORD record
ord-6e06485a7ad2490d9d99f501980827c3
Source dataset
uspto-grants-2002_04
Patent number
US06376499B1

Reaction notes

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