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

HRID 1374926Notes

Reaction equation

HRID 1374926 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 S (−) 2-chloro-1-phenylethanol (2.78 g., 17.8 mmol) and 4,5-dimethylthiazole (2 g., 17.7 mmol) were heated with stirring at 135° C. for 25 hrs. It was cooled to room temperature and water (30 mL) was added to the reaction mixture with stirring. The solution was extracted with ether (30 mL). The ether extract was again extracted with water (30 mL). The combined water layer was evaporated to dryness and the residue was crystallized with a mixture of acetonitrile and methyl tert-butyl ether. Yield: 0.63 g. (7.7%); mp. 189–190° C.; [α]D25−51.765 (Water, c=1.7732).

Workup

  1. temperaturewere heated
  2. temperatureIt was cooled to room temperature
  3. stirringwith stirring
  4. extractionThe solution was extracted with ether (30 mL)
  5. extractionThe ether extract
  6. extractionwas again extracted with water (30 mL)
  7. customThe combined water layer was evaporated to dryness
  8. customthe residue was crystallized with a mixture of acetonitrile and methyl tert-butyl ether

Sources & evidence

ORD record
ord-2867466cd7c545319a872be1a2a20212
Source dataset
uspto-grants-2007_01
Patent number
US07166625B2

Reaction notes

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