Benzyl Bromide → 1-Benzylimidazo[1,2-a]pyridinium bromide

HRID 66011Notes

Reaction equation

HRID 66011 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[Br:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(#N)C>[Br-:10].[CH2:11]([N+:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 78960Imidazo(1,2-a)pyridine

Product 1

HCID 203956171-Benzylimidazo[1,2-a]pyridinium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1.77 g. of imidazo[1,2-a]pyridine in 40 ml. of acetonitrile is added 3.42 g. of α-bromotoluene, and the resulting mixture heated to reflux overnight. The resulting solution is cooled, and the precipitated solids filtered. Recrystallization of the crude product from acetonitrile affords the pure product as a white solid, 2.33 g., m.p. 169°-171° C.

Workup

  1. temperatureto reflux overnight
  2. temperatureThe resulting solution is cooled
  3. filtrationthe precipitated solids filtered
  4. customRecrystallization of the crude product from acetonitrile

Sources & evidence

ORD record
ord-712bf291f749453aa3cb380ac6af7648
Source dataset
uspto-grants-1978_12
Patent number
US04129567

Reaction notes

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