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

HRID 2063

Reaction equation

HRID 2063 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-3a8bce93f6c044b885e4e50a87273179
Source dataset
uspto-grants-1998_03
Patent number
US05728695

Linked notes

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