Water → 2-(4-Isopropoxyphenoxy)-1,3-thiazole

HRID 1028460Notes

Reaction equation

HRID 1028460 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Br[C:13]1[S:14][CH:15]=[CH:16][N:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 820014-Isopropoxyphenol

Product 1

HCID 670969222-(4-Isopropoxyphenoxy)-1,3-thiazoleYield 91.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of Example 1A (15.5 g, 0.1 mol), 2-bromothiazole (18.2 g, 0.11 mol) and potassium carbonate (15.2 g, 0.11 mol) in dimethylsulfoxide was heated at 160° C. under nitrogen for 6 hours. It was then cooled and treated with water, and the aqueous phase was extracted with methylene chloride. The organic layer washed with brine, dried (MgSO4) and concentrated to give 27.5 g of the crude material which was purified on silica gel (5˜35% ethyl acetate in hexane) to afford 21.5 g of the title compound (91% yield) 1H NMR (500 MHz, CDCl3) δ ppm 1.32-1.36 (m, 6 H) 1.34 (none, 6 H) 1.34 (none, 5 H) 4.45-4.57 (m, 1 H) 6.76 (d, J=3.91 Hz, 1 H) 6.87-6.93 (m, 2 H) 7.15-7.20 (m, 2 H) 7.21 (d, J=3.91 Hz, 1 H). MS (ESI): m/z 236 (M−H).

Workup

  1. temperatureIt was then cooled
  2. extractionthe aqueous phase was extracted with methylene chloride
  3. washThe organic layer washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give 27.5 g of the crude material which
  7. customwas purified on silica gel (5˜35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8521ac0bfcee44cc80ddb4321429150a
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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