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

HRID 12461노트

반응식

HRID 12461 반응식
[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]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 19598630HCID 19598630, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-80f85a55b5bb42a9b5fddbc41a2802c1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728009B1

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