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

HRID 967817ノート

反応式

HRID 967817 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d00e08bca188485e84dfc920577aca5b
出典データセット
uspto-grants-2005_10
特許番号
US06956050B2

反応ノート

読み込み中…