Ethanol → Ethyl 1-(4-fluorophenyl)imidazole-5-carboxylate

HRID 30621

反応式

HRID 30621 の反応式
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9]([O:11][CH2:12][CH3:13])=[O:10].C1(C)C(S([CH2:23][N+:24]#[C-:25])(=O)=O)=CC=CC=1.[CH2:27](O)C>>[F:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:27]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:23][N:24]=[CH:25]2)=[CH:4][CH:3]=1

参加物

5

反応物 4

HCID 702EthanolHCID 8025Ethyl formateHCID 97314-FluoroanilineHCID 53627694Toluenesulfonylmethyl isocyanide

生成物 1

HCID 55563221Ethyl 1-(4-fluorophenyl)imidazole-5-carboxylate収率 85%

反応条件

温度
65 °C

実験手順

A mixture of 4-fluoroaniline (11.1 g), ethyl formate (25.0 g) and ethanol (150 ml) was stirred at 65° C. for 2 hrs. Toluenesulfonylmethyl isocyanide (23.4 g) was added to the reaction mixture and the mixture was stirred for 2 hrs. with heating under reflux. The reaction mixture was concentrated and poured into water. The precipitated solids were collected by filtration, washed with water and dried to give ethyl 1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (19.8 g, 85%). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 114-115° C.

後処理

  1. stirringthe mixture was stirred for 2 hrs
  2. temperaturewith heating
  3. temperatureunder reflux
  4. concentrationThe reaction mixture was concentrated
  5. additionpoured into water
  6. filtrationThe precipitated solids were collected by filtration
  7. washwashed with water
  8. customdried

出典と根拠

ORDレコード
ord-4f17b4527f094b85a3aa5846bd4aaa2a
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

関連ノート

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