Acetone → N-[(2-hydroxy)ethyl]-2,4-dimethylthiazolium bromide

HRID 1080184Notes

Reaction equation

HRID 1080184 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.[O:8]1CCO[CH2:10][CH2:9]1.[Br:14]CCO.CC(C)=O>CCOCC>[Br-:14].[OH:8][CH2:9][CH2:10][N+:6]1[C:5]([CH3:7])=[CH:4][S:3][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 180AcetoneHCID 108982-BromoethanolHCID 109342,4-DimethylthiazoleHCID 312751,4-Dioxane

Product 1

HCID 23367180N-[(2-hydroxy)ethyl]-2,4-dimethylthiazolium bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the mixture of 2.4-dimethylthiazole (26.0 g) and dioxane (30 ml) was added 2-bromoethanol (40 g), and the resulting mixture was heated under reflux for 5 hours. To the mixture left standing at room temperature for about 0.5 hour was added acetone (150 ml) with stirring to give pale yellowish white solids. To the mixture was further added ether (150 ml), and the resulting powdery crystals were collected by filtration, washed with acetone and dried under reduced pressure.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. waitTo the mixture left
  4. customto give pale yellowish white solids
  5. filtrationthe resulting powdery crystals were collected by filtration
  6. washwashed with acetone
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c4aaf398ecd4426f9a9669351438d1d8
Source dataset
uspto-grants-1996_12
Patent number
US05580904

Reaction notes

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