Triethylamine → 4-Phenyl-1-(phenylmethyl)-1H-imidazole-2-carbonitrile

HRID 1885831

反応式

HRID 1885831 の反応式
[N:1]#[C:2]Cl.[C:4]1([C:10]2[N:11]=[CH:12][N:13]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:14]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.CCOC(C)=O>C(#N)C>[C:4]1([C:10]2[N:11]=[C:12]([C:2]#[N:1])[N:13]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:14]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10477Cyanogen ChlorideHCID 29274581H-Imidazole, 4-phenyl-1-(phenylmethyl)-

生成物 1

HCID 198779574-Phenyl-1-(phenylmethyl)-1H-imidazole-2-carbonitrile

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

Under nitrogen, 2.0 g (0.0325 ml) cyanogen chloride was added to a 5° C. solution of 6.0 g (0.0256 mol) 4-phenyl-1-(phenylmethyl)-1H-imidazole in 100 ml acetonitrile/10 ml DMF. After 18 hour, the dark yellow reaction was warmed at 70° C. for 7 hours. After cooling, 4.5 ml (0.0325 mol) triethylamine was added and the reaction stirred overnight. The reaction was quenched with 300 ml saturated NaHCO3 and extracted into ethyl acetate (3×150 ml). After drying and concentration, a tan oil was obtained. Flash chromatography (500 ml silica gel, EtOAc) gave 3.7 g recovered starting material and 2.26 g of the desired product (84% based on recovered starting material) mp 95°-96° C. (cyclohexane).

後処理

  1. customthe dark yellow reaction
  2. temperatureAfter cooling
  3. customThe reaction was quenched with 300 ml saturated NaHCO3
  4. extractionextracted into ethyl acetate (3×150 ml)
  5. customAfter drying
  6. concentrationconcentration
  7. customa tan oil was obtained
  8. customrecovered

出典と根拠

ORDレコード
ord-d7203e6f53a74c109ead9dccf259f21f
出典データセット
uspto-grants-1992_09
特許番号
US05147863

関連ノート

読み込み中…