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

Diethyl squarate → 6-chloro-3-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamide

HRID 1050986
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1050986
[Cl:1][C:2]1[C:7]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[C:6]([OH:13])[C:5]([N+:14]([O-])=O)=[CH:4][CH:3]=1.[H][H].[CH2:19]([O:21][C:22]1[C:23](=O)[C:24](=[O:29])[C:25]=1[O:26]CC)[CH3:20]>CO.O.[Pt]=O>[Cl:1][C:2]1[C:7]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[C:6]([OH:13])[C:5]([NH:14][C:23]2[C:24](=[O:29])[C:25](=[O:26])[C:22]=2[O:21][CH2:19][CH3:20])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 123228Diethyl squarateHCID 895256866-chloro-2-hydroxy-N,N-dimethyl-3-nitrobenzamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 895255256-chloro-3-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamideAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 86587499
Platinum oxide monohydrate
Katalysator
HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 5.96 g (24.4 mmol, 1 eq) of 6-chloro-2-hydroxy-N,N-dimethyl-3-nitrobenzamide in 100 ml of methanol in the presence of 0.58 g of platinum oxide hydrate was stirred at hydrogen atmospheric pressure for 3 hours. The reaction medium was filtered through celite and the filtrate was concentrated. The solution obtained was added dropwise to 8.0 g (48.8 mmol, 2 eq) of 3,4-diethoxy-3-cyclobutene-1,2-dione in solution in 50 ml of methanol. The reaction medium was stirred at ambient temperature for 18 hours. The solvent was evaporated off and the residue was chromatographed on silica gel (300 g prepacked column, eluent heptane/acetone, from 50 to 100% of acetone). 4.42 g of 6-chloro-3-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamide were obtained in the form of a beige solid. Yield=54%.

Aufarbeitung

  1. filtrationThe reaction medium was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe solution obtained
  4. customThe solvent was evaporated off
  5. customthe residue was chromatographed on silica gel (300 g prepacked column, eluent heptane/acetone, from 50 to 100% of acetone)

Quellen und Nachweise

ORD-Eintrag
ord-33fd98a876244630a1563718dd61f43b
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09388149B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion