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Acetic Acid → HCID 15698056, Verbindung

HRID 847053
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 847053
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:21]([CH:22]=[O:23])=[C:20]([Cl:24])[N:19]=[C:18]2[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:12][CH:11]=1)([OH:3])=[O:2].[C-]#N.[Na+].[C:32](O)(=[O:34])C>CO.[O-2].[O-2].[Mn+4]>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:16][N:17]2[C:21]([C:22]([O:34][CH3:32])=[O:23])=[C:20]([Cl:24])[N:19]=[C:18]2[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:14][CH:15]=1)([OH:3])=[O:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 11625408HCID 11625408, Verbindung

Produkt 1

HCID 15698056HCID 15698056, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 887
Methanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a mixture of 1.45 g of 1-[(2'-carboxybiphenyl-4-yl)methyl]-2-butyl-4-chloroimidazole-5-carboxaldehyde and 0.91 g of sodium cyanide in 20 mL of methanol at 25° C. was added 0.32 mL of acetic acid followed by 7.25 g of manganese dioxide. The resulting mixture was stirred at 25° C. for 40 hours. The reaction mixture was filtered through Celite®, and the filtrate diluted with water. The aqueous solution was adjusted to pH 3 using hydrochloric acid and extracted with methylene chloride. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was recrystallized from diethyl ether to afford 0.90 g of methyl 1-[(2'-carboxybiphenyl-4-yl)methyl]-2-butyl-4-chloroimidazole-5-carboxylate (m.p. 154°-155° C.). NMR (200 MHz, DMSO-d6); δ12.75 (br s, 1H), 7.73 (d, 1H) 7.58 (t, 1H), 7.46 (t, 1H), 7.34 (m, 3H), 7.07 (d, 2H), 5.63 (s, 2H), 3.78 (s, 3H), 2.67 (t, 2H), 1.56 (quint., 2H), 1.29 (sext., 2H), 0.83 (t, 3H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite®
  2. additionthe filtrate diluted with water
  3. extractionextracted with methylene chloride
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c68bd00a1b19415e9fd151f0469b2c38
Quelldatensatz
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05138069

Notizen zur Reaktion

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