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

HRID 2063

반응식

HRID 2063 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-3a8bce93f6c044b885e4e50a87273179
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728695

연결된 노트

불러오는 중…