Methyl iodide → HCID 66788194, compound

HRID 1253925Notes

Reaction equation

HRID 1253925 reaction equation
IC.[Br:3][C:4]1[C:5]([Cl:14])=[CH:6][C:7]2[O:11][C:10](=[O:12])[NH:9][C:8]=2[CH:13]=1.[C:15](=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O>[Br:3][C:4]1[C:5]([Cl:14])=[CH:6][C:7]2[O:11][C:10](=[O:12])[N:9]([CH3:15])[C:8]=2[CH:13]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 66798091HCID 66798091, compound

Product 1

HCID 66788194HCID 66788194, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Iodomethane (0.579 ml . . . , 926 mmol) was added dropwise to a mixture of 5-bromo-6-chlorobenzo[d]oxazol-2(3H)-one (1.15 g, 4.63 mmol), potassium carbonate (1.599 g, 11.57 mmol) in DMSO (5 mL) at room temperature. The resulting mixture was stirred at this temperature for 18 h. Ethyl acetate (40 mL) was added and the mixture was stirred for 30 min and then filtered. The solution was washed with water (10 mL), brine (15 mL) and dried over Na2SO4. After filtration and concentration, a pale white solid was obtained (1.1 g). 1HNMR (400.342 MHz) δ 3.38 (s, 1H), 7.33 (s, 1H).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. filtrationfiltered
  3. washThe solution was washed with water (10 mL), brine (15 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customa pale white solid was obtained (1.1 g)

Sources & evidence

ORD record
ord-650c75d106144da09262bdb32ec4c550
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

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