Hydrogen Peroxide → 1-Benzyl-5-hydroxymethyl-1H-imidazole

HRID 987197

反応式

HRID 987197 の反応式
[CH2:1]([N:8]1[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[C:9]1S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.[OH-].[Na+]>CO.O[W](O)(=O)=O>[CH2:1]([N:8]1[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 1785198455-Hydroxymethyl-2-mercapto-1-benzylimidazole

生成物 1

HCID 27732351-Benzyl-5-hydroxymethyl-1H-imidazole収率 69%

試薬・触媒・溶媒 2

HCID 1152Tungstic acid触媒HCID 887Methanol溶媒

反応条件

温度
40 °C

実験手順

1-Benzyl-2-mercapto-5-hydroxymethylimidazole(2.2 g, 9.99 mmol) and tungstic acid(H2WO4, 25 mg, 1 mol %) were mixed in 11 ml of methanol. The mixture was warmed to 40° C. in a water bath and 30% hydrogen peroxide(3.75 g, 3.2 molar eq.) was added dropwise thereto for 5 minutes while stirring. The reaction mixture was warmed to 65° C. and refluxed, and stirred at the same temperature for 2.5 hours. Upon exhaustion of the starting material, the mixture was cooled in an ice bath and thereto was added 1 N sodium hydroxide solution(18 ml) to adjust pH of the mixture to 10. The resulting solid was further stirred for 15 minutes, filtered, washed twice with 15 ml of distilled water and 15 ml of isopropyl ether, respectively, and dried to give 1.3 g(Yield 69%, HPLC purity 96.7%) of the title compound as a white powder.

後処理

  1. temperatureThe reaction mixture was warmed to 65° C.
  2. temperaturerefluxed
  3. stirringstirred at the same temperature for 2.5 hours
  4. temperatureUpon exhaustion of the starting material, the mixture was cooled in an ice bath
  5. stirringThe resulting solid was further stirred for 15 minutes
  6. filtrationfiltered
  7. washwashed twice with 15 ml of distilled water and 15 ml of isopropyl ether
  8. customrespectively, and dried

出典と根拠

ORDレコード
ord-f1c09490d0594e029258e665f2465a76
出典データセット
uspto-grants-2003_10
特許番号
US06630593B1

関連ノート

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