Iodoethane → 1-ethyl-2-naphthalen-1-yl-1H-imidazole

HRID 12461ノート

反応式

HRID 12461 の反応式
[H-].[Na+].[C:3]1([C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.I[CH2:19][CH3:20]>CN(C=O)C>[CH2:19]([N:17]1[CH:16]=[CH:15][N:14]=[C:13]1[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)[CH3:20]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 19598630HCID 19598630、化合物

生成物 1

HCID 572422981-ethyl-2-naphthalen-1-yl-1H-imidazole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
50 °C

実験手順

To a suspension of sodium hydride (2.40 g, 60% mineral oil suspension, 60 mmol) in anhydrous DMF (30 ml) is added a solution of 2-naphthalen-1-yl-1H-imidazole (9.70 g, 50 mmol) in DMF (70 ml) at rt. The resulting mixture is stirred at 50° C. for 1 hr, and then cooled to 0° C., after which iodoethane (8.19 g, 52.5 mmol, 1.05 eq.) is added dropwise. The mixture is stirred at rt for 1 hr, and then heated to 50° C. and stirred for an additional 8 hr. The reaction mixture is cooled to rt, and poured into ice-water (500 ml). The mixture is extracted with EtOAc (100 ml×3). The combined organic layers are washed with water and brine, dried over anhydrous sodium sulfate, and solvent is evaporated at reduced pressure. The crude product is purified by flash chromatography on silica gel to give the title compound. LCMS 223 (M+1).

後処理

  1. temperaturecooled to 0° C.
  2. stirringThe mixture is stirred at rt for 1 hr
  3. temperatureheated to 50° C.
  4. stirringstirred for an additional 8 hr
  5. temperatureThe reaction mixture is cooled to rt
  6. extractionThe mixture is extracted with EtOAc (100 ml×3)
  7. washThe combined organic layers are washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate, and solvent
  9. customis evaporated at reduced pressure
  10. customThe crude product is purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-80f85a55b5bb42a9b5fddbc41a2802c1
出典データセット
uspto-grants-2010_06
特許番号
US07728009B1

反応ノート

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