Acetonitrile → 3-(4-Carboxybenzyl)-2,4,5-trimethyloxazolium bromide

HRID 1199332Notes

Reaction equation

HRID 1199332 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.[Br:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=1.C(#N)C>CC(C)=O>[Br-:9].[C:17]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N+:6]2[C:5]([CH3:7])=[C:4]([CH3:8])[O:3][C:2]=2[CH3:1])=[CH:12][CH:13]=1)([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 225994-(Bromomethyl)benzoic acidHCID 302152,4,5-Trimethyloxazole

Product 1

HCID 198663683-(4-Carboxybenzyl)-2,4,5-trimethyloxazolium bromideYield 66.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,4,5-Trimethyloxazole (11.66 g), α-bromo-p-toluic acid (21.5 g), and dry acetonitrile (100 ml) were combined and refluxed for 14 hours under nitrogen with constant stirring. Upon cooling to room temperature, the reaction mixture solidified. The solid was diluted with 100 ml acetone and filtered. The collected solid was slurried in 400 ml refluxing acetone for 20 minutes and filtered while hot. The collected solid was again slurried in 400 ml refluxing acetone and filtered while hot. This solid was washed with 100 ml acetone, then 100 ml ligroin P950 and dried to yield 21.6 g 3-(4-carboxybenzyl)-2,4,5-trimethyloxazolium bromide (Intermediate F).

Workup

  1. temperaturerefluxed for 14 hours under nitrogen with constant stirring
  2. filtrationfiltered
  3. temperaturerefluxing acetone for 20 minutes
  4. filtrationfiltered while hot
  5. temperaturerefluxing acetone
  6. filtrationfiltered while hot
  7. washThis solid was washed with 100 ml acetone
  8. customand dried

Sources & evidence

ORD record
ord-6ca7d50ead4a4e12af96bbfdb750f6ef
Source dataset
uspto-grants-1990_02
Patent number
US04900653

Reaction notes

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