Water → HCID 67096922, compound

HRID 404863Notes

Reaction equation

HRID 404863 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 67096922HCID 67096922, compoundYield 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 six hours. After cooling and treating with water, the aqueous phase was extracted with dichloromethane. The organic layer was washed with brine, dried, and concentrated to give 27.5 g of the crude as a dark brown oil, which was purified on a silica gel (ethyl acetate/hexane 5-35%) to afford 21.5 g of the product as a brown oil (91% yield) 1H NMR (500 MHz, CDCl3) δ ppm 1.32-1.36 (m, 6H) 1.34 (none, 6H) 1.34 (none, 5 H) 4.45-4.57 (m, 1H) 6.76 (d, J=3.91 Hz, 1H) 6.87-6.93 (m, 2H) 7.15-7.20 (m, 2H) 7.21 (d, J=3.91 Hz, 1H). MS (ESI): m/z 236 (M+H).

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give 27.5 g of the crude as a dark brown oil, which
  7. customwas purified on a silica gel (ethyl acetate/hexane 5-35%)

Sources & evidence

ORD record
ord-41af5234463e4d3aacf4624e236ccc55
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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