Methyl iodide → 5-Acetyl-3-methyl-1,3-benzoxazol-2(3H)-one

HRID 1045364Notes

Reaction equation

HRID 1045364 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[NH:9][C:8]=2[CH:13]=1)(=[O:3])[CH3:2].CI.[C:16](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[N:9]([CH3:16])[C:8]=2[CH:13]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 151135715-Acetyl-1,3-benzoxazol-2(3H)-one

Product 1

HCID 151714605-Acetyl-3-methyl-1,3-benzoxazol-2(3H)-oneYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Acetylbenzo[d]oxazol-2(3H)-one (0.5 g, 2.82 mmol), methyl iodide (0.6 g, 4.23 mmol), and cesium carbonate (1.37 g, 4.23 mmol) were dissolved in DMF (2 mL). The reaction mixture was irradiated by microwave for 30 minutes at 100° C. The solvent was removed and extracted with dichloromethane. Purification by silica chromatography (ISCO) produced 5-acetyl-3-methylbenzo[d]oxazol-2(3H)-one (0.4 g, 74%). 1H NMR (400 MHz, CDCl3): δ 7.89 (d, 1H), 7.80 (s, 1H), 7.00 (d, 1H), 3.48 (s, 3H), 2.60 (s, 3H); MS (ESI) m/z: Calculated for C10H9NO3: 191.1. found: 192.1 (M+H)+.

Workup

  1. customThe reaction mixture was irradiated by microwave for 30 minutes at 100° C
  2. customThe solvent was removed
  3. extractionextracted with dichloromethane
  4. customPurification by silica chromatography (ISCO)

Sources & evidence

ORD record
ord-b221930699384098bd7ae15e6a51af5e
Source dataset
uspto-grants-2013_10
Patent number
US08569282B2

Reaction notes

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