Methyl iodide → 5-Bromo-2-(methylthio)benzo[d]oxazole

HRID 1815756Notes

Reaction equation

HRID 1815756 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[S:10])[NH:7][C:6]=2[CH:11]=1.[C:12](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([S:10][CH3:12])=[N:7][C:6]=2[CH:11]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 106331975-Bromo-1,3-benzoxazole-2-thiol

Product 1

HCID 224957925-Bromo-2-(methylthio)benzo[d]oxazoleYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-Bromo-3H-benzooxazole-2-thione (530 mg, 2.30 mmol) was dissolved in DMF (5.75 mL). Potassium carbonate (318 mg, 2.30 mmol) and iodomethane (172 μL, 2.76 mmol) were added and the reaction mixture was allowed to stir at RT for 3.5 h. The mixture was diluted with water (10 mL) and extracted with ethyl acetate (4×10 mL): The combined organic extracts were washed with water (3×10 mL), brine (10 mL) and dried (Na2SO4), filtered and concentrated to afford 538 mg (96%) of the title compound as a dark brown solid:

Workup

  1. extractionextracted with ethyl acetate (4×10 mL)
  2. washThe combined organic extracts were washed with water (3×10 mL), brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-28751d5e0a9f4309aef9f08fac12a04d
Source dataset
uspto-grants-2005_04
Patent number
US06881734B2

Reaction notes

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