Methyl iodide → 5-Acetyl-1,3-Dimethyl-1H-Benzo[D]Imidazol-2(3H)-One

HRID 1045355Notes

Reaction equation

HRID 1045355 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=O)[NH:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[CH3:14]I.[C:16](=[O:19])([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH3:14])[C:16](=[O:19])[N:10]([CH3:9])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 132887695-Acetyl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 171392895-Acetyl-1,3-Dimethyl-1H-Benzo[D]Imidazol-2(3H)-OneYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Acetyl-1H-benzo[d]imidazol-2(3H)-one (1 g, 5.67 mmol), methyl iodide (3.22 g, 22.71 mmol), and cesium carbonate (4.62 g, 14.19 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-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one (0.95 g, 82%). 1H NMR (400 MHz, CDCl3): δ 7.79 (d, 1H), 7.61 (s, 1H), 7.00 (d, 1H), 3.50 (s, 6H), 2.62 (s, 3H); MS (ESI) m/z: Calculated for C11H12N2O2: 204.1. found: 205.2 (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-52c26f88fbd146ef87fa136aac3fe572
Source dataset
uspto-grants-2013_10
Patent number
US08569282B2

Reaction notes

Loading…