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2-Methylimidazole → 1-(4-chloro-2-methoxybenzyl)-2-methyl-1H-imidazole

HRID 272745
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HRID 272745 반응식
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[H-].[Na+].Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[O:18][CH3:19]>CN(C=O)C.C(OCC)(=O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])=[C:12]([O:18][CH3:19])[CH:13]=1
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참가 물질

6

반응물 3

HCID 127492-MethylimidazoleHCID 24758Sodium hydrideHCID 223274741-(Bromomethyl)-4-chloro-2-methoxybenzene

생성물 1

HCID 570132771-(4-chloro-2-methoxybenzyl)-2-methyl-1H-imidazole수율 40%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate
용매

실험 절차

2-Methyl imidazole (45 mg, 0.55 mmol) was dissolved in DMF. Sodium hydride (60 mg, 1.5 mmol) was added slowly. The mixture was stirred at room temperature until bubbling ceased. 1-Bromomethyl-4-chloro-2-methoxy-benzene (117 mg, 0.5 mmol) was added and the mixture was heated to 100° C. for 16 hours. The mixture was cooled to room temperature, diluted with ethyl acetate, and washed with water and with brine. The organic layer was dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel (1:1 hexanes/ethyl acetate) to provide 47 mg (40%) of the title compound. MS (ESI) m/e 237 (M+H)+.

후처리

  1. customuntil bubbling
  2. temperaturethe mixture was heated to 100° C. for 16 hours
  3. temperatureThe mixture was cooled to room temperature
  4. washwashed with water and with brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash column chromatography on silica gel (1:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-499cdbbb45b546f9b3dd8b3932a6f146
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07456169B2

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