Acetic Acid → 3-[1-(4-Aminobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

HRID 653928ノート

反応式

HRID 653928 の反応式
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH:15]=[CH:16][OH:17])=[C:12]([Cl:18])[N:11]=[C:10]2[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:6][CH:5]=1)([O-])=O.C(O)(=O)C>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH:15]=[CH:16][OH:17])=[C:12]([Cl:18])[N:11]=[C:10]2[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:23][CH:24]=1

参加物

5

反応物 2

HCID 176Acetic AcidHCID 665771703-[1-(4-Nitrobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

生成物 1

HCID 665771723-[1-(4-Aminobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

A mixture of 0.2 g of 3-[1-(4-nitrobenzyl)-2-butyl-4-chloroimidazole-5-yl]propen-1-ol, 0.15 g of iron and 0.3 mL of glacial acetic acid in 10 mL of absolute ethanol was refluxed for 1 hour. The reaction mixture was concentrated to dryness and the residue was dissolved in 20 mL of water and the solution was made basic to pH 8 by adding K2CO3. The mixture was then extracted with ehtyl acetate and the ethyl acetate layer was washed with water. The organic layer was concentrated to give a crude product which was purified by flash silica gel column chromatography (ethyl acetate elution). A pure product was obtained as an amorphous solid; NMR (200 MHz, CDCl2): δ 6.76 and 6.62 (dd, 4H, J=8.5 Hz); 6.42-622 (m, 2H); 2.57 (t, 2H, J=7.3 Hz); 1.65 (m, 2H); 1.33 (m, 2H); 0.87 (t, 2H, J=7.3 Hz).

後処理

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in 20 mL of water
  4. additionby adding K2CO3
  5. extractionThe mixture was then extracted with ehtyl acetate
  6. washthe ethyl acetate layer was washed with water
  7. concentrationThe organic layer was concentrated

出典と根拠

ORDレコード
ord-02ca97753e014a11aa00a65af7f102ad
出典データセット
uspto-grants-1992_07
特許番号
US05128355

反応ノート

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