Potassium Hydroxide → 4-Methoxy-1-(3-methyl-3-nitro-butyl)-1,3-dihydro-benzimidazol-2-one

HRID 33390Notes

Reaction equation

HRID 33390 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9](C(OCC)=O)[C:10](=[O:12])[NH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-].[K+].IC[CH2:22][CH2:23][C:24]([CH3:29])([N+:26]([O-:28])=[O:27])[CH3:25]>CN(C=O)C.O>[CH3:1][O:2][C:3]1[C:8]2[NH:9][C:10](=[O:12])[N:11]([CH2:22][CH2:23][C:24]([CH3:29])([N+:26]([O-:28])=[O:27])[CH3:25])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 99430631-Iodo-4-methyl-4-nitro-pentaneHCID 57435847HCID 57435847, compound

Product 1

HCID 671879584-Methoxy-1-(3-methyl-3-nitro-butyl)-1,3-dihydro-benzimidazol-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

4.0 g (17 mmol) ethyl 7-methoxy-2-oxo-2,3-dihydro-benzimidazol-1-carboxylate in DMF are combined with 85% potassium hydroxide solution (3.3 g, 51 mmol) while being cooled with the ice bath. After 30 minutes a solution of 5.2 g (21 mmol) 1-iodo-4-methyl-4-nitro-pentane in DMF is added and the mixture is stirred overnight at ambient temperature. The reaction mixture is diluted with water and extracted with ethyl acetate. The combined organic phases are washed with water, dried and freed from the solvent. The oil remaining is purified by chromatography on a silica gel column (cyclohexane/ethyl acetate gradient). Yield: 0.5 g (8%); mass spectroscopy: [M+H]+=366.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases are washed with water
  3. customdried
  4. customThe oil remaining is purified by chromatography on a silica gel column (cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-ae836f710f6a476cbf4df2fdefba403f
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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