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

HRID 2063

反応式

HRID 2063 の反応式
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

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178418488HCID 178418488、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-3a8bce93f6c044b885e4e50a87273179
出典データセット
uspto-grants-1998_03
特許番号
US05728695

関連ノート

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