Dimethyl Sulfoxide → 1H-Benzimidazole, 2-[[[4-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]-3,5-dimethyl-2-pyridinyl]methyl]thio]-

HRID 1645680Notes

Reaction equation

HRID 1645680 reaction equation
CS(C)=O.CC(C)([O-])C.[K+].[SH:11][C:12]1[NH:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1.C(O[CH2:25][C:26]1[C:31]([CH3:32])=[C:30]([O:33][CH2:34][CH:35]2[CH2:40][O:39][C:38]([CH3:42])([CH3:41])[O:37][CH2:36]2)[C:29]([CH3:43])=[CH:28][N:27]=1)(=O)C>C1(C)C=CC=CC=1>[CH3:41][C:38]1([CH3:42])[O:39][CH2:40][CH:35]([CH2:34][O:33][C:30]2[C:29]([CH3:43])=[CH:28][N:27]=[C:26]([CH2:25][S:11][C:12]3[NH:16][C:15]4[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=4[N:13]=3)[C:31]=2[CH3:32])[CH2:36][O:37]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 23665647Potassium tert-butoxideHCID 59792553HCID 59792553, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 248807801H-Benzimidazole, 2-[[[4-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]-3,5-dimethyl-2-pyridinyl]methyl]thio]-Yield 68.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

To a dimethylsulfoxide (10 ml) solution of potassium t-butoxide (262 mg, 2.33 mmol) and 2-mercaptobenzimidazole (349 mg, 2.33 mmol), (4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl acetate (500 mg, 1.55 mmol) was added and the mixture was stirred in a nitrogen atmosphere at 150° C. for 3 hours and 10 minutes. After cooled to room temperature, the reaction mixture was diluted with toluene and washed with a diluted aqueous sodium hydroxide solution and a saturated saline solution, dried over sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure. The residue was subjected twice to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1) to obtain the title compound (441 mg, 68.8%) as a white foam.

Workup

  1. temperatureAfter cooled to room temperature
  2. washwashed with a diluted aqueous sodium hydroxide solution
  3. dry with materiala saturated saline solution, dried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washThe residue was subjected twice to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-36657a0d10584239a77d64a57251564d
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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