4-Nitrobenzoic Acid → HCID 86742196, Verbindung

HRID 1253246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253246
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:17][C@@H:18]([C@@H:26]1[C@@:30]2([CH3:47])[CH2:31][CH2:32][C@@:33]34[CH2:39][C@:38]53[CH2:40][CH2:41][C@H:42]([OH:46])[C:43]([CH3:45])([CH3:44])[C@@H:37]5[CH2:36][CH2:35][C@H:34]4[C@:29]2([CH3:48])[CH2:28][CH2:27]1)[CH2:19][CH2:20][C:21]([CH3:25])=[C:22]([CH3:24])[CH3:23]>O1CCOCC1>[CH3:17][C@@H:18]([C@@H:26]1[C@@:30]2([CH3:47])[CH2:31][CH2:32][C@@:33]34[CH2:39][C@:38]53[CH2:40][CH2:41][C@H:42]([OH:46])[C:43]([CH3:45])([CH3:44])[C@@H:37]5[CH2:36][CH2:35][C@H:34]4[C@:29]2([CH3:48])[CH2:28][CH2:27]1)[CH2:19][CH2:20][C:21]([CH3:25])=[C:22]([CH3:23])[CH3:24].[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O-:10])=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 61084-Nitrobenzoic AcidHCID 24386Thionyl ChlorideHCID 13920164Cyclobranol

Produkt 1

HCID 86742196HCID 86742196, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To p-nitrobenzoic acid (1 g, 0.006 mole) dissolved in dioxane (20 ml) was added thionyl chloride (3 ml, 7 equivalents) and the mixture was stirred at 60° C. for 2 hours. The resulting mixture was evaporated under reduced pressure, then dioxane (20 ml) and pyridine (3 ml) were added to the resulting residue. Cyclobranol (2 g, 0.0045 mole) was added to the solution and the mixture was stirred at 60° C. for 2 hours to complete the reaction. The mixture was evaporated under reduced pressure, and the residue was extracted with chloroform (30 ml). The extract was washed successively with 3% aqueous sodium carbonate, water, and saturated brine, dried, and evaporated to dryness under reduced pressure. The crude crystals were washed with ethanol (50 ml), and recrystallized from ethyl acetate, giving cyclobranol-p-nitrobenzoate (2.28 g) in a 90% yield. m.p. 244°-245° C.

Aufarbeitung

  1. customThe resulting mixture was evaporated under reduced pressure
  2. additiondioxane (20 ml) and pyridine (3 ml) were added to the resulting residue
  3. stirringthe mixture was stirred at 60° C. for 2 hours
  4. customthe reaction
  5. customThe mixture was evaporated under reduced pressure
  6. extractionthe residue was extracted with chloroform (30 ml)
  7. washThe extract was washed successively with 3% aqueous sodium carbonate, water, and saturated brine
  8. customdried
  9. customevaporated to dryness under reduced pressure
  10. washThe crude crystals were washed with ethanol (50 ml)
  11. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cfac84752a2d409b9a2a26f77cb5fdee
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04748161

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