Pyridine → N-(2-Acetyloxyethyl)-pyridinium Bromide

HRID 248793Notes

Reaction equation

HRID 248793 reaction equation
[C:1]([O:4][CH2:5][CH2:6][Br:7])(=[O:3])[CH3:2].[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(#N)C>[Br-:7].[C:1]([O:4][CH2:5][CH2:6][N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 1049PyridineHCID 135641-Acetoxy-2-bromoethane

Product 1

HCID 19762112N-(2-Acetyloxyethyl)-pyridinium Bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 100.0 grams (0.599 mol) of 2-bromoethyl acetate, 47.37 grams (0.599 mol) of pyridine and 300 milliters of acetonitrile was heated at reflux for 19 hours and then cooled, concentrated on a rotovap to an oil, heated in methyl ethyl ketone and then cooled. On prolonged standing, solid crystallized, was collected and dried. The yield of product was 129.5 grams (87.85% of theory); mp=69°-74° C.

Workup

  1. temperatureat reflux for 19 hours
  2. temperaturecooled
  3. concentrationconcentrated on a rotovap to an oil
  4. temperatureheated in methyl ethyl ketone
  5. temperaturecooled
  6. customcrystallized
  7. customwas collected
  8. customdried

Sources & evidence

ORD record
ord-d5488865e85345a6a3ecf5f5fc10ba41
Source dataset
uspto-grants-1993_05
Patent number
US05212035

Reaction notes

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