1,1'-Carbonyldiimidazole → (E)-1-(2-nitrocinnamyl)-3-(4-pyridyl)-2-imidazolidinone

HRID 476998ノート

反応式

HRID 476998 の反応式
[N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1/[CH:6]=[CH:7]/[CH2:8][NH:9][CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)([O-:3])=[O:2].[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>O1CCCC1.C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1/[CH:6]=[CH:7]/[CH2:8][N:9]1[CH2:10][CH2:11][N:12]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:23]1=[O:24])([O-:3])=[O:2]

参加物

5

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 14834211(E)-N-(2-nitrocinnamyl)-N'-(4-pyridyl)ethylenediamine

生成物 1

HCID 14834212(E)-1-(2-nitrocinnamyl)-3-(4-pyridyl)-2-imidazolidinone収率 56.8%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2.33 g of (E)-N-(2-nitrocinnamyl)-N'-(4-pyridyl)ethylenediamine dissovled in a mixture of 50 ml of tetrahydrofuran and 50 ml of chloroform was added 1.52 g of carbonyldiimidazole at 0° C. The mixture was stirred at room temperature for 40 hours. The solvent was distilled off under reduced pressure, and the residue was extracted with chloroform. The chloroform layer was washed with water, dried and the solvent was distilled off. The residue was purified by silica gel column chromatography (solvent: chloroform-methanol=3:1) and recrystallized from a mixture of isopropanol and methanol to give 1.44 g of (E)-1-(2-nitrocinnamyl)-3-(4-pyridyl)-2-imidazolidinone.

後処理

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (solvent: chloroform-methanol=3:1)
  7. customrecrystallized from a mixture of isopropanol and methanol

出典と根拠

ORDレコード
ord-2237052f4b014ba79cbcea855a00cea6
出典データセット
uspto-grants-1989_12
特許番号
US04886817

反応ノート

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