6-(2-Benzyloxy-ethoxy)-1-methyl-1,3-dihydro-benzoimidazol-2-one → 6-(2-Hydroxy-ethoxy)-1-methyl-1,3-dihydro-benzoimidazol-2-one

HRID 1955253Notes

Reaction equation

HRID 1955253 reaction equation
C([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:19][C:18](=[O:20])[N:17]([CH3:21])[C:16]=2[CH:22]=1)C1C=CC=CC=1>[Pd].CO.O1CCCC1>[OH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:19][C:18](=[O:20])[N:17]([CH3:21])[C:16]=2[CH:22]=1

Participants

5

Reactant 1

HCID 232944866-(2-Benzyloxy-ethoxy)-1-methyl-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 232945396-(2-Hydroxy-ethoxy)-1-methyl-1,3-dihydro-benzoimidazol-2-oneYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(2-benzyloxy-ethoxy)-1-methyl-1,3-dihydro-benzoimidazol-2-one (0.69 g, 2.31 mmol) and 20% palladium on carbon (0.10 g) in methanol (10 ml) and tetrahydrofuran (10 ml) was stirred under a hydrogen atmosphere (1 atm) for 2 h. After removal of the catalyst, the catalyst was washed with boiling methanol (50 ml). The filtrate was evaporated to give 6-(2-hydroxy-ethoxy)-1-methyl-1,3-dihydro-benzoimidazol-2-one (0.46 g, 96%) as a solid. 1H NMR (DMSO) 10.54 (1H, s), 6.78 (1H, d, J=8.3), 6.70 (H, d, J=632.2), 6.50 (1H, dd, J=8.3, 2.4), 4.79 (1H, t, J=5.6), 3.90 (2H, t, J=5.0), 3.64 (2H, q, J=5.2), 3.18 (3H, s).

Workup

  1. customAfter removal of the catalyst
  2. washthe catalyst was washed with boiling methanol (50 ml)
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-310467ec61b74eb08ac8318d9d734efb
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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