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

HRID 442009Notes

Reaction equation

HRID 442009 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 isopropanoldiethyl 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 isopropanoldiethyl ether, 3.8 g

Sources & evidence

ORD record
ord-6082cb4d2be8439f9ff325e2e3daaa5e
Source dataset
uspto-grants-1977_08
Patent number
US04044015

Reaction notes

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