Acetic Acid → 7-(1-Ethylpropyl)-2-(mesitylmethyl)-1-methyl-1H-benzimidazole

HRID 1665229Notes

Reaction equation

HRID 1665229 reaction equation
[CH2:1]([C:3]([C:6]1[C:11]2[N:12]([CH3:25])[C:13]([CH2:15][C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=3[CH3:24])=[N:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[CH:4][CH3:5])[CH3:2].C(O)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:25])[C:13]([CH2:15][C:16]3[C:17]([CH3:24])=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=3[CH3:22])=[N:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 674389407-[1-Ethylprop-1-en-1-yl]-2-(mesitylmethyl)-1-methyl-1H-benzimidazole

Product 1

HCID 249864327-(1-Ethylpropyl)-2-(mesitylmethyl)-1-methyl-1H-benzimidazoleYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7-[1-ethylprop-1-en-1-yl]-2-(mesitylmethyl)-1-methyl-1H-benzimidazole (110 mg, 0.331 mmol) in tetrahydrofuran (3.5 mL) was added a solution of borane-dimethyl sulfide complex in tetrahydrofuran (1.9 M, 3.5 mL, 6.63 mmol) at 0° C. After the reaction mixture was stirred at room temperature for 15 hr, acetic acid (5.0 mL) was added to the mixture and the mixture was heated at 120° C. for 2 hr. After the reaction mixture was cooled, the mixture was poured into saturated aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (50 mL, twice). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 10-25% ethyl acetate/n-hexane gradient mixture to give the title compound (12 mg, 0.0359 mmol, 11%) as a colorless solid.

Workup

  1. temperaturethe mixture was heated at 120° C. for 2 hr
  2. temperatureAfter the reaction mixture was cooled
  3. extractionextracted with ethyl acetate (50 mL
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with 10-25% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-e3b674f2f3d544e599ea4fdf39515489
Source dataset
uspto-grants-2011_10
Patent number
US08039500B2

Reaction notes

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