4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 7303349, compound

HRID 556702Notes

Reaction equation

HRID 556702 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][CH2:8][OH:9].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:9][CH2:8][CH2:7][C:6]2[S:5][CH:4]=[N:3][C:2]=2[CH3:1])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 7303349HCID 7303349, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-5-thiazoleethanol (2 mL, 16.7 mmol) in CH2Cl2 (10 mL) and pyridine (10 mL) was added p-toluenesulfonyl chloride (3.5 g, 18.4 mmol) portionwise over 15 min. This mixture was stirred at ambient temperature for 18 h then was quenched with 5% aqueous HCl (15 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 50% hexanes/ethyl acetate) to give 2-(4-methylthiazol-5-yl)ethyl 4-methylbenzenesulfonate (3.24 g, 10.9 mmol, 65% yield). MS (DCI/NH3) m/z 298 (M+H)+.

Workup

  1. customthen was quenched with 5% aqueous HCl (15 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 mL)
  4. dry with materialThe combined organics were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified via column chromatography (SiO2, 50% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-2640f90f23da4f928df16ef2b0753a2a
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

Loading…