Water → 5-Bromo-2-(2H-tetrazol-5-yl)pyridine

HRID 1966925Notes

Reaction equation

HRID 1966925 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][N:4]=1)#[N:2].[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[NH:10]1[C:1]([C:3]2[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][N:4]=2)=[N:2][N:12]=[N:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 8171545-Bromopyridine-2-carbonitrile

Product 1

HCID 234386835-Bromo-2-(2H-tetrazol-5-yl)pyridineYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

10 g of 2-cyano-5-bromopyridine prepared in the Preparation example 5 was dissolved in 100 ml of dimethylformamide, 5.33 g of sodiumazide, and 4.4 g of ammoniumchloride were added to the solution at room temperature, and the solution was stirred at the temperature of 110° C. for 3 hours for reaction. The reaction mixture was added with water and then was extracted with ethyl acetate. The organic layer, thus separated, was washed with brine, dehydrated, filtrated and concentrated in vacuo thereby to obtain 10.5 g of the title compound. Yield 85%.

Workup

  1. extractionwas extracted with ethyl acetate
  2. customThe organic layer, thus separated
  3. washwas washed with brine
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9fe13dac3ad4424baa6e0cc96261a6a
Source dataset
uspto-grants-2013_04
Patent number
US08420676B2

Reaction notes

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