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

HRID 66014Notes

Reaction equation

HRID 66014 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-0faca37a6e124296a96b2b3064178b99
Source dataset
uspto-grants-1978_12
Patent number
US04129567

Reaction notes

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