Water → 1-[4-(2-azidoethyl)phenyl]-2-ethyl-4-phenyl-1H-imidazole

HRID 967817노트

반응식

HRID 967817 반응식
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:12]=[C:11]2[CH2:21][CH3:22])=[CH:6][CH:5]=1.[N-:23]=[N+:24]=[N-:25].[Na+].O>CN(C=O)C>[N:23]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:12]=[C:11]2[CH2:21][CH3:22])=[CH:6][CH:5]=1)=[N+:24]=[N-:25]

참가 물질

5

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 222914291-[4-(2-chloroethyl)phenyl]-2-ethyl-4-phenyl-1H-imidazole

생성물 1

HCID 222913861-[4-(2-azidoethyl)phenyl]-2-ethyl-4-phenyl-1H-imidazole수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 1-[4-(2-chloroethyl)phenyl]-2-ethyl-4-phenyl-1H-imidazole (1.1 g, 3.4 mmol) and KI (566 mg, 3.4 mmol) in DMF (7 mL) was added sodium azide (443 mg, 6.8 mmol), and then the resulting mixture was stirred overnight at 100° C. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried (MgSO4). After removal of solvent, the crude product was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (2:1) to afford 960 mg (89%) of the title compound as pale yellow amorphous: MS (ESI) m/z 318 [M+H]+, 1H-NMR (CDCl3)δ1.26 (2H, t, J=7.5 Hz), 2.72 (3H, q, J=7.7 Hz), 2.98 (2H, t, J=6.6 Hz), 3.59 (2H, t, J=6.6 Hz), 7.20-7.41 (9H, m), 7.79 (2H, dd, J=7.1, 1.3 Hz).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customAfter removal of solvent
  5. customthe crude product was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (2:1)

출처 및 근거

ORD 기록
ord-d00e08bca188485e84dfc920577aca5b
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956050B2

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