Dimethyl Sulfoxide → HCID 12509111, compound

HRID 1851675Notes

Reaction equation

HRID 1851675 reaction equation
CS(C)=O.[NH:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13](Br)[CH:12]=1.[OH-].[K+]>C(OC(=O)C)C>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([N:5]2[CH:9]=[CH:8][N:7]=[CH:6]2)[CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 795ImidazoleHCID 14797Potassium HydroxideHCID 891432-Bromo-4-methylanisole

Product 1

HCID 12509111HCID 12509111, compoundYield 57%

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 4-methyl-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 solid (57%). 1H-NMR (300 MHz, CDCl3) δ(ppm) 7.78 (s, 1H), 7.16 (m, 3H), 7.09 (d, J=1.8 Hz, 1H), 6.94 (d, J=8.4 Hz, 1H), 3.81 (s, 3H), 2.33 (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-21be4d39fbbf4d78a47648a3b5dd6b25
Source dataset
uspto-grants-2015_02
Patent number
US08957217B2

Reaction notes

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