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

HRID 1645677Notes

Reaction equation

HRID 1645677 reaction equation
CC1C=CC(S(O[CH2:12][C:13]2[C:18]([CH3:19])=[C:17]([O:20][CH2:21][CH:22]3[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24][CH2:23]3)[C:16]([CH3:30])=[CH:15][N:14]=2)(=O)=O)=CC=1.[SH:31][C:32]1[NH:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=1.C(N(CC)CC)C.[OH-].[Na+]>C1(C)C=CC=CC=1.O1CCCC1>[CH3:29][C:25]1([CH3:28])[O:24][CH2:23][CH:22]([CH2:21][O:20][C:17]2[C:16]([CH3:30])=[CH:15][N:14]=[C:13]([CH2:12][S:31][C:32]3[NH:36][C:35]4[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=4[N:33]=3)[C:18]=2[CH3:19])[CH2:27][O:26]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 59792411(4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl 4-methylbenzenesulfonateHCID 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 96.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl 4-methylbenzenesulfonate (457 mg, 1.05 mmol), 2-mercaptobenzimidazole (158 mg, 1.05 mmol), and tetrahydrofuran (5 ml), triethylamine (0.293 ml, 2.1 mmol) was added and the mixture was stirred at room temperature for 15 hours and 30 minutes. To the reaction mixture, toluene and a diluted aqueous sodium hydroxide solution were added and the organic layer was taken out. The aqueous layer was extracted again with toluene. The organic layers were combined and washed with a saturated saline solution, dried over sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure. The residue was dissolved in n-heptane/ethyl acetate (1/1) and subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1→0/1) to obtain the title compound (419 mg, 96.5%) as a colorless viscous oil.

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted again with toluene
  3. washwashed with a saturated saline solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in n-heptane/ethyl acetate (1/1)
  8. washsubjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1→0/1)

Sources & evidence

ORD record
ord-2517de27ef604cc5b855fdbf3b9d4a2a
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

Loading…