Sodium Hydroxide → 5-(Oxiran-2-yl)-2-(1H-tetrazol-1-yl)pyridine

HRID 2281319Notes

Reaction equation

HRID 2281319 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)=[N:7][CH:8]=1)=[CH2:2].BrN1C(=[O:20])CCC1=O.[OH-].[Na+]>O.CC(O)(C)C>[O:20]1[CH2:2][CH:1]1[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 895451885-Ethenyl-2-(tetrazol-1-yl)pyridine

Product 1

HCID 895436045-(Oxiran-2-yl)-2-(1H-tetrazol-1-yl)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 5-ethenyl-2-(1H-tetrazol-1-yl)pyridine (0.664 g, 3.83 mmol) in a 2:1 ratio of H2O:t-BuOH (30 mL) was treated with N-bromosuccinimide in portions over 5 minutes (0.751 g, 4.22 mmol, 1.1 equiv) and stirred at 40° C. for 1 hour. After cooling to 5° C., the reaction was basified with drop wise addition of solution of sodium hydroxide (0.46 g in 5 mL of H2O, 11.50 mmol, 3 equiv) and stirred for another 1 hour. The reaction mixture was poured into H2O (10 mL) and the product was precipitated out as white solid, filtered, washed with water, dried, yielding the title compound.

Workup

  1. temperatureAfter cooling to 5° C.
  2. stirringstirred for another 1 hour
  3. customthe product was precipitated out as white solid
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-c97d727cf5c14d4d8c6d7da09cf9dde9
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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