Methyl morpholine oxide → HCID 66697339, compound

HRID 2386785Notes

Reaction equation

HRID 2386785 reaction equation
C[N+]1([O-])CCOCC1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:31])[CH:17]([C:19]2[CH:30]=[CH:29][C:22]3[N:23]([CH3:28])[C:24](=[O:27])[N:25]([CH3:26])[C:21]=3[CH:20]=2)[OH:18])=[C:12]([Cl:32])[CH:11]=1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:31])[C:17]([C:19]2[CH:30]=[CH:29][C:22]3[N:23]([CH3:28])[C:24](=[O:27])[N:25]([CH3:26])[C:21]=3[CH:20]=2)=[O:18])=[C:12]([Cl:32])[CH:11]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67546932HCID 67546932, compound

Product 1

HCID 66697339HCID 66697339, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Methyl-morpholine-4-oxide (280 mg) and tetrapropylammonium perruthenate (36 mg) were added to a solution of 5-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-propyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (424 mg) in DCM (5 ml) with 3A molecular sieves. The mixture was stirred for 3 h at room temperature, filtered over SiO2 (10 g) and concentrated to give the title compound (410 mg) as a white foam. MS (m/e)=409.1 [M+H+].

Workup

  1. filtrationfiltered over SiO2 (10 g)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2ab7a322eebe431199e86b67cb1aca35
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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