Water → Tert.-butyl [6-[3-(1-methylvinyl)-2-oxo-1-benzimidazolinyl]hexyl]carbamate

HRID 1382928Notes

Reaction equation

HRID 1382928 reaction equation
[CH3:1][C:2]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])=[CH2:3].CS(O[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=O)=O.O>CN(C)C=O>[CH3:3][C:2]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:5]1=[O:13])=[CH2:1]

Participants

5

Reactant 3

HCID 962WaterHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-oneHCID 184654786-((tert-Butoxycarbonyl)amino)hexyl methanesulfonate

Product 1

HCID 57066051Tert.-butyl [6-[3-(1-methylvinyl)-2-oxo-1-benzimidazolinyl]hexyl]carbamateYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5.9 g (135 mmol) of a 55% sodium hydride dispersion in mineral oil are washed oil-free with hexane and subsequently covered with 100 ml of dimethylformamide. To this suspension are added dropwise at room temperature 22.3 g (128 mmol) of 1-(1-methylvinyl)benzimidazolin-2-one in 100 ml of dimethylformamide. After stirring at room temperature for 2 hours 55.0 g of tert.-butyl [6-[(methylsulphonyl)oxy]hexyl]carbamate in 100 ml of dimethylformamide are added dropwise and the reaction mixture is stirred at room temperature for 18 hours. Thereafter. the reaction mixture is poured into 1 l of water and extracted with 750 ml of methylene chloride. The organic extract is washed with water, dried over potassium carbonate and evaporated. The thus-obtained residue is chromatographed on 950 g of silica gel with methylene chloride/hexane, methylene chloride and a 95:5 mixture of methylene chloride and isopropanol as the elution agent, whereby there are obtained 45.3 g of tert.-butyl [6-[3-(1-methylvinyl)-2-oxo-1-benzimidazolinyl]hexyl]carbamate as an oil.

Workup

  1. wash5.9 g (135 mmol) of a 55% sodium hydride dispersion in mineral oil are washed oil-free with hexane
  2. additionare added dropwise
  3. extractionextracted with 750 ml of methylene chloride
  4. extractionThe organic extract
  5. washis washed with water
  6. dry with materialdried over potassium carbonate
  7. customevaporated
  8. customThe thus-obtained residue is chromatographed on 950 g of silica gel with methylene chloride/hexane, methylene chloride
  9. additiona 95:5 mixture of methylene chloride and isopropanol as the elution agent, whereby there

Sources & evidence

ORD record
ord-460071627ed44ef7818bfec8e837ad93
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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