4-Methoxybenzenecarboximidamide → 2-(4-Methoxyphenyl)-4-(2-nitrophenyl)imidazole

HRID 1871269

反応式

HRID 1871269 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])=O.[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[NH:21])=[CH:18][CH:17]=1>C(#N)C>[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]2[NH:22][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N+:11]([O-:13])=[O:12])[N:21]=2)=[CH:18][CH:17]=1

参加物

4

反応物 2

HCID 2290744-MethoxybenzenecarboximidamideHCID 2440252-Bromo-2'-nitroacetophenone

生成物 1

HCID 1784889232-(4-Methoxyphenyl)-4-(2-nitrophenyl)imidazole収率 78.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
40 °C

実験手順

A mixture of 2-bromo-2'-nitroacetophenone (18 g), 4-methoxybenzamidine (20 g), and silica gel (20 g) in acetonitrile (500 ml) is heated at 40° C. for 24 hours. The reaction is evaporated and the residue put on a layer of silica gel and eluted with 50% ethyl acetate/hexane (1500 ml). The solution is evaporated under reduced pressure to approximately 250 ml and extracted with 5% HCl (3×250 ml) . The combined aqueous solution is basified with K2CO3 and extracted with ethyl acetate (3×400 ml) to afford 2-(4-methoxyphenyl)-4-(2-nitrophenyl)-imidazole (17 g) as a dark yellow oil which is used in the next step without further purification.

後処理

  1. customThe reaction is evaporated
  2. washthe residue put on a layer of silica gel and eluted with 50% ethyl acetate/hexane (1500 ml)
  3. customThe solution is evaporated under reduced pressure to approximately 250 ml
  4. extractionextracted with 5% HCl (3×250 ml)
  5. extractionextracted with ethyl acetate (3×400 ml)

出典と根拠

ORDレコード
ord-0268b124d7274ac985604a8b37b9ab91
出典データセット
uspto-grants-2000_08
特許番号
US06103731

関連ノート

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