4,5-Dimethylthiazole → Thiazolium, 3-(2-hydroxy-2-phenylethyl)-4,5-dimethyl-, chloride

HRID 989912Notes

Reaction equation

HRID 989912 reaction equation
[Cl:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[CH3:11][C:12]1[N:13]=[CH:14][S:15][C:16]=1[CH3:17]>O>[Cl-:1].[C:5]1([CH:3]([OH:4])[CH2:2][N+:13]2[C:12]([CH3:11])=[C:16]([CH3:17])[S:15][CH:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 625104,5-DimethylthiazoleHCID 928982-Chloro-1-phenylethanol

Product 1

HCID 9838299Thiazolium, 3-(2-hydroxy-2-phenylethyl)-4,5-dimethyl-, chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

The neat mixture of 2-chloro-l-phenylethanol (2.34 g, 14.9 mmole) and 4,5-dimethylthiazole (1.69 g, 14.9 mmole) were heated with stirring at 135° C. for 28 hrs. It was cooled to room temperature and water (30 mL) was added to the reaction mixture with stirring, and then was extracted with ether (30 mL). The water layer was treated with actived carbon and evaporated to dryness. It was crystallized from a mixture of acetonitrile and ether to give a racemic product as prisms; 0.39 g (9.7%); mp. 201-203° C.

Workup

  1. temperaturewere heated
  2. temperatureIt was cooled to room temperature
  3. stirringwith stirring
  4. extractionwas extracted with ether (30 mL)
  5. additionThe water layer was treated with actived carbon
  6. customevaporated to dryness
  7. customIt was crystallized from a mixture of acetonitrile and ether

Sources & evidence

ORD record
ord-6bfc94e3239146c2931353c484c5939a
Source dataset
uspto-grants-2002_10
Patent number
US06458819B1

Reaction notes

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