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

HRID 1288834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1288834
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 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-bbb858a4ae6f4ec3868ae9f52c40c35b
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05747491

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