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

HRID 1670888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670888
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 1-[(4-methylphenyl)sulfonyl]-2-phenyl-1H-imidazole-4-carbaldehyde (300 mg), methylammonium chloride (225 mg), molecular sieves 3A (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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-791078fc3cca454899b23d3a4b822f3e
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994205B2

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