Acetonitrile → 1-Benzyl-6-chloroimidazo[1,2-a]pyridinium bromide

HRID 261115Notes

Reaction equation

HRID 261115 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[Br:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(#N)C>C(OCC)C>[Br-:11].[CH2:12]([N+:10]1[CH:9]=[CH:8][N:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=12)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 27643286-Chloroimidazo(1,2-a)pyridine

Product 1

HCID 203955731-Benzyl-6-chloroimidazo[1,2-a]pyridinium bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2.3 g. of 6-chloroimidazo[1,2-a]pyridine and 3.42 g. of α-bromotoluene in 40 ml. of dry acetonitrile is heated at reflux temperatures overnight. The solution is cooled and 35 ml. of diethyl ether added. The precipitated solids are collected and twice recrystallized from isopropanol-diethyl ether, 3.8 g., m.p. 193°-195° C.

Workup

  1. temperatureat reflux temperatures overnight
  2. temperatureThe solution is cooled
  3. customThe precipitated solids are collected
  4. customtwice recrystallized from isopropanol-diethyl ether, 3.8 g

Sources & evidence

ORD record
ord-0acab4bbb1c44328b8b7d4b097046ffd
Source dataset
uspto-grants-1979_08
Patent number
US04163745

Reaction notes

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