Methyl iodide → 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole

HRID 1857695

反応式

HRID 1857695 の反応式
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27]I.[OH-].[Na+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][CH2:9][C:10]1[N:11]([CH3:27])[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 1784190342-Benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole

生成物 1

HCID 221305032-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole収率 22%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

In 50 ml of dry tetrahydrofuran was dissolved 15 g (44 mmol) of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (16a). To this solution was added 6.87 g (48.4 mmol) of methyl iodide under ice-cooling, further followed by addition of 1.94 g (48.4 mmol) of sodium hydroxide and 100 mg of tetrabutylammonium bromide. After the ice-water bath was removed, the mixture was stirred for 1 hour. This reaction mixture was concentrated under reduced pressure and the residue was neutralized with hydrochloric acid and sodium hydrogen carbonate to be weakly basic and extracted twice with ethyl acetate. The pooled organic layer was washed with water and dried over sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was fractionated by silica gel chromatography (3% ethyl acetate in methylene chloride). From the first fraction, 3.5 g (yield 22%) of the objective position isomer (17a') was obtained as oil. From the subsequent fraction, 10.4 g (yield 67%) of the objective 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (17a) was obtained as oil.

後処理

  1. temperaturecooling
  2. customAfter the ice-water bath was removed
  3. concentrationThis reaction mixture was concentrated under reduced pressure
  4. extractionextracted twice with ethyl acetate
  5. washThe pooled organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure

出典と根拠

ORDレコード
ord-3dd2006a7aae42428919d3fbba9df829
出典データセット
uspto-grants-2000_11
特許番号
US06147097

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