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

HRID 31728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31728
CS(O[CH2:6][C:7]1[C:12]([CH3:13])=[C:11]([O:14][CH2:15][CH:16]2[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]2)[C:10]([CH3:24])=[CH:9][N:8]=1)(=O)=O.[SH:25][C:26]1[NH:27][C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=1.C(N(CC)CC)C>O1CCCC1>[CH3:23][C:19]1([CH3:22])[O:18][CH2:17][CH:16]([CH2:15][O:14][C:11]2[C:10]([CH3:24])=[CH:9][N:8]=[C:7]([CH2:6][S:25][C:26]3[NH:30][C:29]4[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=4[N:27]=3)[C:12]=2[CH3:13])[CH2:21][O:20]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 59792581(4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl methanesulfonateHCID 178527775HCID 178527775, Verbindung

Produkt 1

HCID 248807801H-Benzimidazole, 2-[[[4-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]-3,5-dimethyl-2-pyridinyl]methyl]thio]-Ausbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of (4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl methanesulfonate (500 mg, 1.39=mmol), 2-mercaptobenzimidazole (209 mg, 1.39 mmol) and tetrahydrofuran (5 ml), triethylamine (0.387 ml, 2.78 mmol) was added and the mixture was stirred at room temperature for 14 hours and 25 minutes. The reaction mixture was concentrated under reduced pressure, and toluene and a 0.1N aqueous sodium hydroxide solution were added to the residue and insoluble substance was removed by filtration. The organic layer was taken out and the aqueous layer was extracted again with toluene. The organic layers were combined, 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 (549 mg, 95.5%) as a colorless viscous oil.

Aufarbeitung

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and toluene
  3. additiona 0.1N aqueous sodium hydroxide solution were added to the residue and insoluble substance
  4. customwas removed by filtration
  5. extractionthe aqueous layer was extracted again with toluene
  6. washwashed with a saturated saline solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltrated
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. dissolutionThe residue was dissolved in n-heptane/ethyl acetate (1/1)
  11. washsubjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1→0/1)

Quellen und Nachweise

ORD-Eintrag
ord-3767c2328b404813ada50a0be46e5052
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

Notizen zur Reaktion

Wird geladen…