Iodoethane → 1-Ethyl-4-methyl-1,3-dihydrobenzimidazol-2-one

HRID 1176616Notes

Reaction equation

HRID 1176616 reaction equation
[CH3:1][C:2]1[C:10]2[NH:9][C:8](=[O:11])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:14](I)[CH3:15].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:14]([N:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:10]=2[NH:9][C:8]1=[O:11])[CH3:15]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 125019744-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one

Product 1

HCID 684988521-Ethyl-4-methyl-1,3-dihydrobenzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 17.10 g of 4-methyl-1,3-dihydrobenzimidazol-2-one in 250 ml of anhydrous N,N-dimethylformamide is admixed at 0° C. with 4.070 g of sodium hydride dispersion (60%). The reaction mixture is stirred at 0° C. over a further 30 minutes and 7.5 ml of ethyl iodide are added dropwise. The reaction mixture is stirred at 30° C. over 14 hours, poured onto 500 ml of saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate (2×500 ml). The combined organic phases are washed with 500 ml of brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a brown solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (200:5:1 dichloromethane-methanol-25% conc. ammonia); Rt=3.17.

Workup

  1. stirringThe reaction mixture is stirred at 30° C. over 14 hours
  2. extractionextracted with ethyl acetate (2×500 ml)
  3. washThe combined organic phases are washed with 500 ml of brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-9d771eda18114ad086a447e72658d5d8
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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