StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

2,4,5-Trimethoxybenzaldehyde → N-cyclohexyl-N-cyclopentyl-4-[hydroxy(2,4,5-trimethoxyphenyl)methyl]benzamide

HRID 1588929
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1588929
Br[C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1.C([Li])(C)(C)C.[CH3:27][O:28][C:29]1[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH3:40])=[CH:33][C:30]=1[CH:31]=[O:32]>C1COCC1>[CH:14]1([N:8]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6](=[O:7])[C:5]2[CH:20]=[CH:21][C:2]([CH:31]([OH:32])[C:30]3[CH:33]=[C:34]([O:39][CH3:40])[C:35]([O:37][CH3:38])=[CH:36][C:29]=3[O:28][CH3:27])=[CH:3][CH:4]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 205252,4,5-TrimethoxybenzaldehydeHCID 197548884-bromo-N-cyclohexyl-N-cyclopentylbenzamideHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 19754870N-cyclohexyl-N-cyclopentyl-4-[hydroxy(2,4,5-trimethoxyphenyl)methyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a cold (-70° C.), stirred solution of 4-bromo-N-cyclohexyl-N-cyclopentylbenzamide (1.5 g, 4.3 mmol) in THF (20 ml) was added slowly a solution of tertbutyllithium (5 ml of 1.7 M solution in pentane) under an Argon atmosphere. The reaction was stirred at -70° to -75° for 20 min. and a solution of 2,4,5-trimethoxybenzaldehyde (843 mg, 4.3 mmol) in THF (10 ml) was added dropwise over 30 min. The reaction was stirred at -70° to -75° for 30 min. and at room temperature for 1 hr. The reaction was quenched by the addition of water and the aqueous layer extracted three times with ethyl acetate. The combined organic layers were washed with water and dried (Na2SO4). The drying agent was filtered and the filtrate concentrated in vacuo to give the crude product. Purification was effected by chromatography on silica gel using mixtures of ethyl acetate and hexane. The product was isolated as a glass.

Aufarbeitung

  1. stirringThe reaction was stirred at -70° to -75° for 30 min. and at room temperature for 1 hr
  2. customThe reaction was quenched by the addition of water
  3. extractionthe aqueous layer extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationThe drying agent was filtered
  7. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5d0d7e9bff4f43be89c0f6c5c292cc33
Quelldatensatz
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05223539

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion