Cyanamide → 2-[4-(2-amino-5-methyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethanol

HRID 967810

Reaktionsgleichung

Reaktionsgleichung von HRID 967810
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]([CH3:20])[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)=[CH:6][CH:5]=1.[N:21]#[C:22][NH2:23]>C(O)C>[NH2:23][C:22]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][OH:1])=[CH:5][CH:6]=2)[C:11]([CH3:20])=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:21]=1

Komponenten

4

Edukt 2

HCID 9864CyanamideHCID 222913492-{[4-(2-Hydroxyethyl)phenyl]amino}-1-phenyl-1-propanone

Produkt 1

HCID 222913562-[4-(2-amino-5-methyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethanolAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-{[4-(2-hydroxyethyl)phenyl]amino}-1-phenyl-1-propanone (1.3 g, 5.0 mmol) and cyanamide (420 mg, 10 mmol) in ethanol (60 mL) was refluxed for 16 h. After removal of solvent, the residue was diluted with dichloromethane. The organic layer was washed with water, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/ethanol (10:1) to give 490 mg (33%) of the title compound as yellow solids: 1H-NMR (CDCl3) δ 2.16 (3H, s), 2.96 (2H, t, J=5.6 Hz), 3.96 (2H, t, J=5.6 Hz), 4.24 (1H, br), 7.29-7.21 (2H, m), 7.46-7.38 (4H, m), 7.66-7.63 (2H, m).

Aufarbeitung

  1. temperaturewas refluxed for 16 h
  2. customAfter removal of solvent
  3. additionthe residue was diluted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/ethanol (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-d09fb717b79d46d3afa64cdcd2f4be1c
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956050B2

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