Methanol → HCID 66987468, compound

HRID 555275Notes

Reaction equation

HRID 555275 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:19]=[CH:18][C:8]2[N:9]([CH2:12][CH2:13][O:14][CH2:15]SC)[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4].O[O:21][S:22]([O-:24])=O.[K+].[CH3:26]O>O>[CH3:1][O:2][C:3]([C:5]1[CH:19]=[CH:18][C:8]2[N:9]([CH2:12][CH2:13][O:14][CH2:15][S:22]([CH3:26])(=[O:24])=[O:21])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 66987547HCID 66987547, compound

Product 1

HCID 66987468HCID 66987468, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(2-methylsulfanylmethoxyethyl)-1H-benzimidazole-5-carboxylic acid methyl ester (3.0 g. 10.7 mmoles) in methanol (30 mL) was cooled to 0° C. and to this was added a solution of oxone (4.88 g, 7.94 mmoles) in water. The solution was stirred at the ambient temperature for 12 h. It was quenched with 5% sodium bicarbonate solution and extracted with EtOAc. Removal of solvent gave 2.0 g (60%) of 1-(2-methane-sulfonylmethoxy-ethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester. MS-ESI m/z 313(M+1): 1H NMR (300 MHz, DMSO-d6) δ 2.9 (s, 3H), 4.0 (s, 3H), 4.25 (t, 2H), 4.65 (t, 2H), 4.75 (s, 2H), 7.85 (d, 2H), 8.0 (dd, 1H), 8.35 (s, 1H), 8.5 (s, 1H)

Workup

  1. customIt was quenched with 5% sodium bicarbonate solution
  2. extractionextracted with EtOAc
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-8f5a8258fd7b448a8b58a52633fa2dd3
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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