Potassium Carbonate → 2-(4-Isopropoxyphenoxy)-1,3-thiazole

HRID 2078448Notes

Reaction equation

HRID 2078448 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+]>CS(C)=O.C(OCC)(=O)C>[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 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 820014-Isopropoxyphenol

Product 1

HCID 670969222-(4-Isopropoxyphenoxy)-1,3-thiazoleYield 55%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 4-isopropoxyphenol (CAS #7495-77-4. 3 g, 19.7 mmole), at room temperature in DMSO (30 mL) was added in turn, 2-bromothiazole (3.23 g, 19.7 mmole) and potassium carbonate (5.44 g, 39.4 mmole), heated at 160° C. for 3 hours. The reaction mixture was cooled, diluted with ethyl acetate, washed with water and brine sequentially, dried over magnesium sulfate, filtered and concentrated. The residue was purified on Silica gel column using a gradient of 5 to 25% ethyl acetate in hexane and provided 2.54 g (55%) of the title compound as yellowish oil. 1H NMR (300 MHz, CDCl3) δ ppm 7.22 (d, J=3.68 Hz, 1H) 7.15-7.21 (m, 2H) 6.86-6.95 (m, 2H) 6.76 (d, J=4.04 Hz, 1H) 4.43-4.60 (heptet, J=6.25 Hz, 1H) 1.34 (d, J=6.25 Hz, 6H). MS (ESI) m/z 236 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water and brine sequentially
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on Silica gel column

Sources & evidence

ORD record
ord-25dbe31636ab47bc90d16c2f977c8582
Source dataset
uspto-grants-2011_04
Patent number
US07928243B2

Reaction notes

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