Dicyclohexylcarbodiimide → Ethyl (E)-3-[4-(1-imidazolylmethyl)phenyl]-2-propen-1-yl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

HRID 1975591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1975591
[CH3:1][C:2]1[NH:3][C:4]([CH3:25])=[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]=1[C:8](O)=[O:9].[NH:26]1[CH:30]=[CH:29][N:28]=[C:27]1[CH2:31][C:32]1[CH:37]=[CH:36][C:35](/[CH:38]=[CH:39]/[CH2:40][OH:41])=[CH:34][CH:33]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[CH3:25][C:4]1[NH:3][C:2]([CH3:1])=[C:7]([C:8]([O:41][CH2:40]/[CH:39]=[CH:38]/[C:35]2[CH:36]=[CH:37][C:32]([CH2:31][C:27]3[NH:26][CH:30]=[CH:29][N:28]=3)=[CH:33][CH:34]=2)=[O:9])[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:5]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 46567273-Ethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylateHCID 21648924(E)-3-[4-(1-imidazolylmethyl)phenyl]-2-propen-1-ol

Produkt 1

HCID 21650171Ethyl (E)-3-[4-(1-imidazolylmethyl)phenyl]-2-propen-1-yl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

346 mg (1 mM) of 1,4-dihydro-2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)pyridine-3-caboxylic acid together with 215 mg (1 mM) of (E)-3-{4-(1-imidazolylmethyl)phenyl}-2-propen-1-ol, 248 mg (1.2 mM) of dicyclohexylcarbodiimide and 134 mg (1.1 mM) of 4-N,N-dimethylaminopyridine were dissolved in 5 ml of toluene, while heating, and refluxed for six hours. The solution was cooled to room temperature, and the crystals produced were filtered off. The filtrate was washed with water and dried over anhydrous sodium sulfate. After the solvent was distilled away, the residue was purified by chromatography on a silica gel column, whereby the captioned compound was obtained. The yield was 474 mg (87.4%).

Aufarbeitung

  1. temperaturewhile heating
  2. temperaturerefluxed for six hours
  3. customthe crystals produced
  4. filtrationwere filtered off
  5. washThe filtrate was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter the solvent was distilled away
  8. customthe residue was purified by chromatography on a silica gel column, whereby the captioned compound
  9. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-7917357d089140e7963f38368bfd4a2e
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05286869

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