Hydrochloric Acid → 1-[2-Chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine hydrochloride

HRID 554415ノート

反応式

HRID 554415 の反応式
[Cl:1][C:2]1[N:3]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH:7]=O.CO.[CH3:26][NH2:27].[BH4-].[Na+].Cl.C(=O)([O-])O.[Na+]>CO>[ClH:1].[Cl:1][C:2]1[N:3]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH2:7][NH:27][CH3:26]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 862328822-Chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

生成物 1

HCID 669248561-[2-Chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine hydrochloride収率 121.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2-Chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (440 mg) was dissolved in methanol (20 mL), 40% methylamine methanol solution (494 mg) was added at room temperature, and the mixture was stirred for 30 min. Sodium borohydride (144 mg) was added at room temperature, and the mixture was stirred for 10 min. 1 mol/L Hydrochloric acid (20 mL) was added, and the mixture was stirred for 5 min. The reaction mixture was alkalized with a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=3:7→0:1), and dissolved in ethyl acetate (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 ethyl acetate to give the title compound as colorless crystals (yield 308 mg, 61%).

後処理

  1. stirringthe mixture was stirred for 10 min
  2. stirringthe mixture was stirred for 5 min
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=3:7→0:1)
  8. dissolutiondissolved in ethyl acetate (5 mL)
  9. additionA 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added
  10. concentrationthe mixture was concentrated under reduced pressure
  11. customThe residue was crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-968dddd0ccdc43958ef27536ccf58788
出典データセット
uspto-grants-2011_11
特許番号
US08048909B2

反応ノート

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