Sodium hydride → HCID 86735281、化合物

HRID 461462

反応式

HRID 461462 の反応式
[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[N:22]=[CH:23][S:24][CH:25]=1>O1CCCC1.O>[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[N:22]=[CH:23][S:24][CH:25]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 27632904-(Chloromethyl)-1,3-thiazole2 回

生成物 1

HCID 86735281HCID 86735281、化合物収率 92.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

A solution of 1-(2,4-dichloro-phenyl)-2-(1-imidazolyl) ethanol (2.4 g, 9.4 mmole) in dry tetrahydrofuran (20 ml) was added to sodium hydride (0.62 g, as an 80% dispersion in oil, 0.02 mole) and warmed at 70° C for 90 minutes. The solution was cooled to 0° C and 4-chloromethylthiazole (1.5 g, 11.2 mmole), dissolved in a little dry tetrahydrofuran, was added. The mixture was stirred at 0° C for 1 hour and at room temperature for 6 hours. Further 4-chloromethylthiazole (0.25 g) was added and the stirring continued for 36 hours. The reaction mixture was then diluted with water (70 ml) and extracted several times with ether. The ether extracts were combined, dried over MgSO4 and evaporated. The oily residue was taken up in dry ether (50 ml) and treated with a solution of HCl in ether. The solid precipitate was collected and recrystallized from a mixture of methanol and di-isopropyl ether to give 1-[2,4-dichloro-β-(4-thiazolylmethoxy) phenethyl]imidazole hydrochloride (1.7 g, 46%) m.p. 183°-184°. (Found: C, 46.3; H, 3.7; N, 10.7. C15H13N3Cl2OS.HCl requires C, 46.1; H, 3.6; N, 10.7%).

後処理

  1. temperatureThe solution was cooled to 0° C
  2. additionwas added
  3. waitthe stirring continued for 36 hours
  4. extractionextracted several times with ether
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. additiontreated with a solution of HCl in ether
  8. customThe solid precipitate was collected
  9. customrecrystallized from a mixture of methanol and di-isopropyl ether

出典と根拠

ORDレコード
ord-def45323cb3d433197a0a26f4a50ada9
出典データセット
uspto-grants-1977_12
特許番号
US04062966

関連ノート

読み込み中…