Water → HCID 69170730, compound

HRID 1028468Notes

Reaction equation

HRID 1028468 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[C:11]1[S:12][CH:13]=[CH:14][N:15]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 764302-Bromothiazole

Product 1

HCID 69170730HCID 69170730, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-methoxyphenol (5.50 g, 44.3 mmol, 1.1 eq.), 2-bromothiazole (6.64 g, 40.0 mmol, 1.0 eq.), and K2CO3 (6.60 g, 47.8 mmol, 1.2 eq.) in dimethyl sulfoxide (40 mL) was heated to 160° C. for 5 hours. The reaction mixture was poured into water and extracted with ether. The ether layer washed with 10% NaOH, then brine, dried over MgSO4, filtered and concentrated. The residue was purified on silica gel eluting with ethyl acetate:hexane (0-20%) to give the title compound (6.03 g, 73%),

Workup

  1. extractionextracted with ether
  2. washThe ether layer washed with 10% NaOH
  3. dry with materialbrine, dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-68af5d6d14f44c17bbccdf810db26745
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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