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

HRID 476998노트

반응식

HRID 476998 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2237052f4b014ba79cbcea855a00cea6
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886817

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