Tetrahydrofuran → 7-(1-Ethyl-1-hydroxypropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 1698554Notes

Reaction equation

HRID 1698554 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][N:6]1[C:10]2[C:11]([C:15]([O:17]C)=O)=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:19].O1CC[CH2:22][CH2:21]1>>[CH2:21]([C:15]([C:11]1[C:10]2[N:6]([CH3:5])[C:7](=[O:19])[NH:8][C:9]=2[CH:14]=[CH:13][CH:12]=1)([OH:17])[CH2:1][CH3:2])[CH3:22]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 59635373methyl 1-methyl-2-oxo-1,3-dihydro-2H-benzimidazole-7-carboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 672734887-(1-Ethyl-1-hydroxypropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-oneYield 70%

Conditions

Temperature
40 °C

Procedure

A solution of ethylmagnesium bromide (3M solution in diethyl ether; 32 mL, 96 mmol) was added dropwise to a suspension of methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (5.00 g, 24.2 mmol) in tetrahydrofuran (50 mL) at 0° C. The mixture was stirred at 40° C. overnight. The reaction was quenched with water and 1N HCl, extracted with ethyl acetate, washed with brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was crystallized from ethanol/diethylether to afford the title compound as colorless crystals (3.39 g, 70%). mp 199-201° C.

Workup

  1. customThe reaction was quenched with water and 1N HCl
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from ethanol/diethylether

Sources & evidence

ORD record
ord-98b83b1ab40b4e88a846ae169e9f55bd
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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