1-[[1-(2-Methylsulfanylethyl)benzimidazol-2-yl]methyl]benzotriazole → 1-[[1-(2-Methylsulfonylethyl)benzimidazol-2-yl]methyl]benzotriazole

HRID 1072010Notes

Reaction equation

HRID 1072010 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:14][N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1.[OH2:24].[OH2:25].O.O.O.O.C1(=O)OOOOC(=O)C2=CC=CC=C12.[Mg]>CN(C)C=O.CCOC(C)=O>[CH3:1][S:2]([CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:14][N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1)(=[O:25])=[O:24]

Participants

5

Reactant 2

HCID 52720151-[[1-(2-Methylsulfanylethyl)benzimidazol-2-yl]methyl]benzotriazoleHCID 86596527CID 86596527

Product 1

HCID 52720171-[[1-(2-Methylsulfonylethyl)benzimidazol-2-yl]methyl]benzotriazoleYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[1-(2-Methylthio-ethyl)-1H-benzimidazol-2-ylmethyl]-1H-benzotriazole (100 mg, 0.309 mmol) was dissolved in anhydrous N,N-dimethylformamide (5 mL). Magnesium monoperoxy phthalate hexahydrate (611 mg, 1.24 mmol) was added and the reaction mixture was stirred at room temperature overnight under N2. The solvent was stripped under reduced pressure. The yellow oily residue was taken up in EtOAc (100 mL) and washed with water (2×50 mL) dried over magnesium sulfate, filtered and evaporated. Column chromatography on silica gel (EtOAc) gave 45 mg (41%) of the title compound as an oil.

Workup

  1. washwashed with water (2×50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-9f4ce949c7e34748a0231f25cc8f7b7c
Source dataset
uspto-grants-2005_06
Patent number
US06908936B2

Reaction notes

Loading…