Methanamine, hydrochloride (1:1) → N,N-dimethyl-1-{1-[(4-methylphenyl)sulfonyl]-2-phenyl-1H-imidazol-4-yl}methanamine

HRID 2359961ノート

反応式

HRID 2359961 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:15]=[C:14]([CH:16]=O)[N:13]=[C:12]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl-].[CH3:25][NH3+:26].[BH4-].[Na+].[C:29](=O)([O-])O.[Na+]>C(O)C>[CH3:25][N:26]([CH3:29])[CH2:16][C:14]1[N:13]=[C:12]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:9])=[O:10])[CH:15]=1

参加物

6

反応物 4

HCID 11637Methanamine, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 236606871-[(4-methylphenyl)sulfonyl]-2-phenyl-1H-imidazole-4-carbaldehyde

生成物 1

HCID 57687730N,N-dimethyl-1-{1-[(4-methylphenyl)sulfonyl]-2-phenyl-1H-imidazol-4-yl}methanamine収率 29%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

A mixture of 1-[(4-methylphenyl)sulfonyl]-2-phenyl-1H-imidazole-4-carbaldehyde (300 mg), methylammonium chloride (225 mg), molecular sieves 3 A (2.0 g) and ethanol (10 mL) was stirred at 60° C. for 1 hr. The reaction mixture was cooled, sodium borohydride (105 mg) was added at 5-10° C., and the mixture was stirred for 30 min. Saturated aqueous sodium hydrogen carbonate was added at the same temperature, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=2:3→0:1), and crystallized by adding a solution (10 mL) of anhydrous oxalic acid in ethyl acetate to give the title compound as colorless crystals (yield 106 mg, 29%).

後処理

  1. temperatureThe reaction mixture was cooled
  2. stirringthe mixture was stirred for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=2:3→0:1)
  8. customcrystallized
  9. additionby adding a solution (10 mL) of anhydrous oxalic acid in ethyl acetate

出典と根拠

ORDレコード
ord-26dff72a03474903bd5e5381bd690a11
出典データセット
uspto-grants-2014_04
特許番号
US08686010B2

反応ノート

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