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Water → ethyl 5-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-ylthio]pentanoate

HRID 1033246
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1033246
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([SH:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(=O)([O-])[O-].[K+].[K+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[C:11]([S:22][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[NH:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 178489021HCID 178489021, Verbindung

Produkt 1

HCID 10094797ethyl 5-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-ylthio]pentanoateAusbeute 103,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553
Tetrabutylammonium Iodide
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Part A. A suspension of 4,5-bis(4-methoxyphenyl)-2-mercapto-1H-imidazole (10.4 g, 33.2 mmol), ethyl 5-bromovalerate (5.00 mL, 31.6 mmol), potassium carbonate (5.50 g, 39.8 mmol), and tetra-n-butylammonium iodide (2 g) in tetrahydrofuran (100 mL) was heated to reflux for 20 hours. The mixture was cooled, and poured into water (400 mL). This was extracted with methylene chloride (2 ×400 mL), and the extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual oil was purified by elution through a short plug of silica gel with ethyl acetate, and evaporation afforded ethyl 5-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-ylthio]pentanoate (14.4 g, 32.6 mmol, 98%) as a waxy, low-melting solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. temperatureThe mixture was cooled
  4. extractionThis was extracted with methylene chloride (2 ×400 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residual oil was purified by elution through a short plug of silica gel with ethyl acetate, and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-298db64730b94ab5ab0f0411a5bc672e
Quelldatensatz
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05310748

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