Dimethyl Sulfoxide → HCID 5305516, compound

HRID 1851673Notes

Reaction equation

HRID 1851673 reaction equation
CS(C)=O.[NH:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18].[OH-].[K+]>C(OC(=O)C)C>[N:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 795ImidazoleHCID 113582-BromoanisoleHCID 14797Potassium Hydroxide

Product 1

HCID 5305516HCID 5305516, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a degassed DMSO (20 mL) solution of imidazole (1.0 g, 15 mmol) was added 2-bromoanisole (1.25 mL, 10 mmol), KOH (1.12 g, 20 mmol) and Cu2O (280 mg, 2 mmol) under nitrogen. The resulting mixture was stirred at 140° C. for 24 hrs under N2. After cooling to room temperature, the mixture was poured into ethylacetate (EA) (50 mL) and filtered. The filtrate was washed with water (50 mL×3) and dried over anhydrous magnesium sulfate. After rotary evaporation, the crude oil was purified via column chromatography on silica gel with eluent of EA/MeOH (9/1, v/v), affording a light yellow liquid (50%). 1H-NMR (400 MHz, CDCl3) δ(ppm) 7.79 (s, 1H), 7.36 (t, J=7.8 Hz, 1H), 7.28 (d, J=7.8 Hz, 1H), 7.21 (s, 1H), 7.17 (s, 1H), 7.05 (m, 2H), 3.85 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with water (50 mL×3)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter rotary evaporation
  6. customthe crude oil was purified via column chromatography on silica gel with eluent of EA/MeOH (9/1

Sources & evidence

ORD record
ord-359cad5590ec4dce85078c3586731dda
Source dataset
uspto-grants-2015_02
Patent number
US08957217B2

Reaction notes

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