Sodium Azide → HCID 21696649, compound

HRID 378786Notes

Reaction equation

HRID 378786 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[Cl:13].[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C=O)C.O>[N:14]([C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[Cl:13])=[N+:15]=[N-:16]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 21696603HCID 21696603, compound

Product 1

HCID 21696649HCID 21696649, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4,6-dibromo-3-chloropyridine-2-carboxylate (6.0 g 0.018 mol) in DMF (50 mL) was added sodium azide (2.0 g 0.03 mol) and the solution warmed to 50° C. for 1 hr. The reaction was diluted with water (200 mL) and cooled to 0° C. for 1 hr. The solid was collected to give methyl 4-azido-6-bromo-3-chloropyridine-2-carboxylate (4.4 g, 0.012 mol, 66%); mp 84-86° C.

Workup

  1. temperaturecooled to 0° C. for 1 hr
  2. customThe solid was collected

Sources & evidence

ORD record
ord-6ba5e30a53bd4aaa8eed9824a8c93581
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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