Water → 1-Phenethyl-4-phenyl-imidazole

HRID 1773859노트

반응식

HRID 1773859 반응식
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:14](OS(C)(=O)=O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[CH2:14]([N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[CH:9]1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 146679Methanesulfonic acid, 2-phenylethyl esterHCID 178418822HCID 178418822, 화합물

생성물 1

HCID 572929641-Phenethyl-4-phenyl-imidazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-phenyl-1H-imidazole (1 g, 8.75 mmoles) in DMF (8 mL) is added NaH 60% dispersion in mineral oil (455 mg, 11 mmoles). The reaction mixture is stirred at room temperature for 1 hour, then methanesulfonic acid phenethyl ester (example 4D) (1.84 g, 9.12 mmoles) is added. The reaction mixture is then heated at 60° C. for 2 hours. Water is added, and the aqueous phase is extracted three times with AcOEt. The organic phase is washed with water, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH) (100:0) then (98:2) to give 1-phenethyl-4-phenyl-imidazole.

후처리

  1. temperatureThe reaction mixture is then heated at 60° C. for 2 hours
  2. extractionthe aqueous phase is extracted three times with AcOEt
  3. washThe organic phase is washed with water, brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-8ce6ed6a32b14a03822ba22b74aa1566
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255101B2

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