反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:16])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[H-].[Na+].Cl[CH2:20][C:21]1[S:22][CH:23]=[CH:24][CH:25]=1>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([O:16][CH2:20][C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1参加物
反応条件
- 温度
- 70 °C
実験手順
A solution of 1-(2,4-dichloro-phenyl)-2-(1-imidazolyl) ethanol (1.5 g, 5.8mmole) dissolved in dry tetrahydrofuran (10 ml) was added to a stirred suspension of sodium hydride (0.39 g, as 80% dispersion in oil, 16 mmole) in dry tetrahydrofuran (10 ml) and warmed to 70° C for 90 minutes. The mixture was cooled in ice and a solution of 2-chloromethyl-thiophene (1.16 g, 8.8 mmole) in dry tetrahydrofuran was added. The mixture was heated at 70° for 3 hours and allowed to stir at room temperature overnight. The solvent was removed under vacuum and the residue stirred with dry ether (200 ml). The ether solution was filtered through celite and saturated with hydrogen chloride gas to precipitate an oil which was solidified by trituration with ether and ethylacetate. The solid product was collected and recrystallized from a mixture of acetone and di-isopropyl ether to give 1-[2,4-dichloro-β-(2-thienylmethoxy)phenethyl]imidazole hydrochloride as fine white crystals (0.63 g, 31%) m.p. 153°-154° C. (Found: C, 49.2; H, 3.8; N, 7.3. C16H14Cl2N2OS.HCl requires C, 49.3; H, 3.9; N, 7.2%).
後処理
- temperatureThe mixture was cooled in ice
- temperatureThe mixture was heated at 70° for 3 hours
- customThe solvent was removed under vacuum
- stirringthe residue stirred with dry ether (200 ml)
- filtrationThe ether solution was filtered through celite and saturated with hydrogen chloride gas
- customto precipitate an oil which
- customThe solid product was collected
- customrecrystallized from a mixture of acetone and di-isopropyl ether
出典と根拠
- ORDレコード
- ord-9d7474e7f621458da5add39693f6cf87
- 出典データセット
- uspto-grants-1977_12
- 特許番号
- US04062966
関連ノート
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