Acetic Acid → 5-Bromo-2-(tetrazol-1-yl)pyridine

HRID 2281317Notes

Reaction equation

HRID 2281317 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.C(O)(=O)C.[CH2:13](OC(OCC)OCC)C.[N-:23]=[N+:24]=[N-:25].[Na+]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:13]=[N:25][N:24]=[N:23]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 41365425-Bromo-2-(tetrazol-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 5-bromopyridin-2-amine (5.0 g, 28.9 mmol) in acetic acid (40 ml, 699 mmol) was added (diethoxymethoxy) ethane (7.70 ml, 46.2 mmol), followed by sodium azide (2.82 g, 43.3 mmol). The mixture was heated at 80° C. for 1 hour. The reaction mixture was cooled to room temperature and diluted with water. The resulting precipitate was collected and dried under high vacuum to provide the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe resulting precipitate was collected
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-8a285f428fa24d29bfbf164bc7816e3e
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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