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

HRID 31731ノート

反応式

HRID 31731 の反応式
[CH3:1][C:2]1([CH3:18])[O:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[CH:12][C:11]=2[CH3:17])[CH2:4][O:3]1.[SH:19][C:20]1[NH:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.[OH-].[Na+].[CH3:31]O>>[CH3:1][C:2]1([CH3:18])[O:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[C:11]([CH3:17])=[CH:12][N:13]=[C:14]([CH2:31][S:19][C:20]3[NH:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[N:21]=3)[C:15]=2[CH3:16])[CH2:4][O:3]1

参加物

5

反応物 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 866099724-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridineHCID 178527775HCID 178527775、化合物

生成物 1

HCID 248807801H-Benzimidazole, 2-[[[4-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]-3,5-dimethyl-2-pyridinyl]methyl]thio]-収率 84.9%

実験手順

To a mixture of 2-(chloromethyl)-(4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridine (837 mg, 2.79 mmol), 2-mercaptobenzimidazole (419 mg, 2.79 mmol) and sodium hydroxide (223 mg, 5.58 mmol), methanol (20 ml) was added and the mixture was stirred at room temperature for 12 hours and 55 minutes. The reaction mixture was concentrated under reduced pressure. Toluene and a 0.1N aqueous sodium hydroxide solution were added to the residue and insoluble substance was removed by filtration, and then, 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 (980 mg, 84.9%) as a white foam.

後処理

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionToluene and a 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)

出典と根拠

ORDレコード
ord-dbec951eafcb4b7db903accecd071cd9
出典データセット
uspto-grants-2008_09
特許番号
US07425634B2

反応ノート

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