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

HRID 2194720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194720
C[N:2]([CH2:10][C:11]1[N:12]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:14][CH:15]=1)[C:3](=O)OC(C)(C)C.[H-].[Na+].[Cl:24][CH2:25][S:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1>CN(C)C=O.O>[ClH:24].[ClH:24].[CH3:3][NH:2][CH2:10][C:11]1[N:12]=[C:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:14]([CH2:25][S:26][C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)[CH:15]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 1502059Chloromethyl p-Tolyl SulfideHCID 178482990HCID 178482990, Verbindung

Produkt 1

HCID 68409200N-methyl-1-(1-{[(4-methylphenyl)thio]methyl}-2-phenyl-1H-imidazol-4-yl)methanamine dihydrochlorideAusbeute 8,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl methyl[(2-phenyl-1H-imidazol-4-yl)methyl]carbamate (350 mg) in dimethylformamide (5 mL) was added sodium hydride (60% in oil, 421 mg) and the mixture was stirred for 1 hr. 1-[(Chloromethyl)thio]-4-methylbenzene (316 mg) was added dropwise, and the mixture was stirred at 80° C. for 15 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with water, 3% aqueous potassium hydrogensulfate solution, saturated sodium hydrogen carbonate solution and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1→1:4) and dissolved in methanol (10 mL). A 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added and the mixture was stirred at 75° C. for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate to give the title compound as colorless crystals (yield 31 mg, yield 6.4%).

Aufarbeitung

  1. stirringthe mixture was stirred at 80° C. for 15 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water, 3% aqueous potassium hydrogensulfate solution, saturated sodium hydrogen carbonate solution and saturated brine in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1→1:4)
  7. dissolutiondissolved in methanol (10 mL)
  8. additionA 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added
  9. stirringthe mixture was stirred at 75° C. for 30 min
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. customthe residue was crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fc0c20ae614949e9bd8e7633c6d8f2ca
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334301B2

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