4-Methyl-5-(2-hydroxyethyl)thiazole → 5-(2-Methylsulfonyloxyethyl)-4-methylthiazole

HRID 656279Notes

Reaction equation

HRID 656279 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][CH2:8][OH:9].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([O:9][CH2:8][CH2:7][C:6]1[S:5][CH:4]=[N:3][C:2]=1[CH3:1])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 101049265-(2-Methylsulfonyloxyethyl)-4-methylthiazoleYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-methylthiazol-5-yl)ethanol (5.01 g) was dissolved in dichloromethane (100 ml) and to the solution was added triethylamine (5.06 g), followed by adjusting the temperature of reactor to 0° C. To the obtained solution was added dropwise methanesulfonyl chloride (4.58 g), and the mixture was stirred for 21. hours while allowed to warm up to room temperature. The reaction solution was washed with water, concentrated under reduced pressure, and then purified by column-chromatography (hexane/ethyl acetate=1/3) to yield 5-(2-methylsulfonyloxyethyl)-4-methylthiazole (5.18 g, 67%) as a pale yellow liquid.

Workup

  1. customto 0° C
  2. washThe reaction solution was washed with water
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column-chromatography (hexane/ethyl acetate=1/3)

Sources & evidence

ORD record
ord-00babaff51bf4f519fc3b78317a97508
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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