Sodium Thiosulfate Pentahydrate → N-methyl-1-(1-{[(4-methylphenyl)sulfonyl]methyl}-2-phenyl-1H-imidazol-4-yl)methanamine dihydrochloride

HRID 2194721ノート

反応式

HRID 2194721 の反応式
[ClH:1].Cl.[CH3:3][NH:4][CH2:5][C:6]1[N:7]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:9]([CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:10]=1.OOS([O-])=O.[K+].[OH2:32].[OH2:33].O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>O.CC(C)=O>[ClH:1].[ClH:1].[CH3:3][NH:4][CH2:5][C:6]1[N:7]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:9]([CH2:11][S:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:33])=[O:32])[CH:10]=1

参加物

7

反応物 4

HCID 61475Sodium Thiosulfate PentahydrateHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 68409200N-methyl-1-(1-{[(4-methylphenyl)thio]methyl}-2-phenyl-1H-imidazol-4-yl)methanamine dihydrochloride

生成物 1

HCID 68409474N-methyl-1-(1-{[(4-methylphenyl)sulfonyl]methyl}-2-phenyl-1H-imidazol-4-yl)methanamine dihydrochloride収率 40.7%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒2 回

実験手順

To a solution of N-methyl-1-(1-{[(4-methylphenyl)thio]methyl}-2-phenyl-1H-imidazol-4-yl)methanamine dihydrochloride (250 mg) in water (10 mL) and acetone (10 mL) was added dropwise a solution of oxone (700 mg) in water (20 mL), and the mixture was stirred at room temperature for 3 hr. Sodium thiosulfate pentahydrate (783 mg) was added to the reaction mixture and the mixture was stirred for 24 hr. A saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with a mixed solution of ethyl acetate-tetrahydrofuran (1:1). The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=1:0→7:3) and dissolved in methanol (5 mL). A 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added, and the mixture was concentrated under reduced pressure. The residue was crystallized from tetrahydrofuran to give the title compound as colorless crystals (yield 55 mg, yield 20%).

後処理

  1. stirringthe mixture was stirred for 24 hr
  2. extractionthe mixture was extracted with a mixed solution of ethyl acetate-tetrahydrofuran (1:1)
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=1:0→7:3)
  6. dissolutiondissolved in methanol (5 mL)
  7. additionA 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added
  8. concentrationthe mixture was concentrated under reduced pressure
  9. customThe residue was crystallized from tetrahydrofuran

出典と根拠

ORDレコード
ord-8603c456b0a245d4b84506d01ee0490a
出典データセット
uspto-grants-2012_12
特許番号
US08334301B2

反応ノート

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