Triethylamine → 5-(Azidomethyl)pyridine-2-carbonitrile

HRID 1990750Notes

Reaction equation

HRID 1990750 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1.S(Cl)(C)(=O)=O.C(N(CC)CC)C.S([O-])(=O)(=O)C.[N-:28]=[N+:29]=[N-:30].[Na+]>C(Cl)Cl.CN(C=O)C.O>[N:28]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1)=[N+:29]=[N-:30]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 85257MethanesulfonateHCID 122519662-Cyano-5-hydroxymethylpyridine

Product 1

HCID 219046275-(Azidomethyl)pyridine-2-carbonitrileYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

5-(Hydroxymethyl)pyridine-2-carbonitrile (4 g, 0.03 mol; see step (ii) above) was dissolved in 25 mL of methylene chloride and cooled in an ice bath. Mesyl chloride (2.32 mL, 0.0300 mol) and then triethylamine (4.6 mL, 0.033 mol) were added dropwise. The reaction mixture was stirred and after work up the crude mesylate was treated with NaN3 (7.35 g, 0.113 mol) in 20 mL of DMF. The reaction mixture was stirred at 40° C. for 2 h, diluted with water and extracted with ethyl acetate. The organic layer was concentrated to yield 3.95 g (83%) of the crude azide.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe reaction mixture was stirred at 40° C. for 2 h
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-8c9ec290d5a04cfebf2432e7a135eeb7
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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