4-Toluenesulfonyl chloride → 1H-Imidazole-4-methanol, 1-[(4-methylphenyl)sulfonyl]-

HRID 2063

Reaktionsgleichung

Reaktionsgleichung von HRID 2063
Cl.[OH:2][CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[OH:2][CH2:3][C:4]1[N:5]=[CH:6][N:7]([S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH:8]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178418488HCID 178418488, Verbindung

Produkt 1

HCID 115289461H-Imidazole-4-methanol, 1-[(4-methylphenyl)sulfonyl]-Ausbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Hydroxymethylimidazole hydrochloride (10 g) was suspended in dichloromethane (200 ml). ρ-Toluenesulfonyl chloride (15.58 g) was added and triethylamine (25.8 ml) was added dropwise to the stirred reaction mixture which was allowed to stir at room temperature overnight. The mixture was washed with water (2×100 ml) and brine (1×100 ml) and the organic layer was dried and evaporated to leave a clear oil which was recrystallised from ethyl acetate/hexane to afford the title compound as a white crystalline solid (15 g, 80%). 1H NMR (360 MHz, CDCl3) δ2.44 (3H, s), 4.55 (2H, s), 7.21 (1H, s), 7.35 (2H, d, J=8.0 Hz), 7.62 (2H, d, J=8.0 Hz 7.98 (1H, s). MS (CI+) m/z 253 (M+H, 100%).

Aufarbeitung

  1. washThe mixture was washed with water (2×100 ml) and brine (1×100 ml)
  2. customthe organic layer was dried
  3. customevaporated
  4. customto leave a clear oil which
  5. customwas recrystallised from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-3a8bce93f6c044b885e4e50a87273179
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728695

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