Iodide Ion → 7-(1-Ethylpropyl)-4-methoxy-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 1698560Notes

Reaction equation

HRID 1698560 reaction equation
Br[C:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[C:5]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:4][CH:3]=1.[I-].[CH3:19][O-:20].[Na+]>CO.CN(C)C=O.O>[CH2:14]([CH:13]([C:5]1[C:6]2[N:7]([CH3:12])[C:8](=[O:11])[NH:9][C:10]=2[C:2]([O:20][CH3:19])=[CH:3][CH:4]=1)[CH2:16][CH3:17])[CH3:15]

Participants

7

Reactant 3

HCID 30165Iodide IonHCID 10942334Sodium MethoxideHCID 672727554-bromo-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 672729917-(1-Ethylpropyl)-4-methoxy-1-methyl-1,3-dihydro-2H-benzimidazol-2-oneYield 91%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (250 mg, 0.841 mmol), anhydrous cuprus iodide (192 mg, 1.01 mmol) and 28% sodium methoxide in methanol (5.2 mL) in N,N-dimethylformamide (5 mL) was heated at 100° C. for 1 h. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The organics were dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound (190 mg, 0.765 mmol, 91%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a595cf219eb44013b2a5e68d7db1fa46
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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