Ethyl Acetate → 2-(((3-methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl)sulfinyl)-1H-benzimidazole

HRID 1645518Notes

Reaction equation

HRID 1645518 reaction equation
[CH3:1][C:2]1[C:3]([CH2:19][S:20][C:21]2[NH:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[N:22]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][C:11]1([CH2:16][CH2:17][CH3:18])[O:15][CH2:14][CH2:13][O:12]1.ClC1C=CC=C(C(OO)=[O:38])C=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CO>[CH3:1][C:2]1[C:3]([CH2:19][S:20]([C:21]2[NH:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)=[O:38])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][C:11]1([CH2:16][CH2:17][CH3:18])[O:12][CH2:13][CH2:14][O:15]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 597923962-(((3-methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl)thio)-1H-benzimidazole

Product 1

HCID 597925212-(((3-methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl)sulfinyl)-1H-benzimidazoleYield 64.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Procedure

The 2-(((3-methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl)thio)-1H-benzimidazole (482 mg, 1.17 mmol) obtained in the step (3f) was dissolved in a solvent mixture of toluene (30 ml) and methanol (3 ml). The mixture was cooled in a nitrogen atmosphere. To this mixture, a methanol solution (1.3 ml) of 3-chloroperbenzoic acid (311 mg, 1.17 mmol as the content was regarded as 65%) was added at an inner temperature of below −70° C. and stirred below −60° C. for 2 hours. To the reaction mixture, an aqueous solution of sodium hydrogen carbonate and ethyl acetate were added. The organic layer was separated and washed with a saturated saline solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was dissolved in methylene chloride and subjected to silica gel column chromatography using NH silica gel (elution solvent: methylene chloride/methanol=1/0→100/1→100/5) to obtain the title compound (323 mg, yield: 64.3%).

Workup

  1. temperatureThe mixture was cooled in a nitrogen atmosphere
  2. additionwas added at an inner temperature of below −70° C.
  3. customThe organic layer was separated
  4. washwashed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. dissolutionThe residue was dissolved in methylene chloride

Sources & evidence

ORD record
ord-edfb06f084a04961b400f821e9be4a2a
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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