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

3-Methoxyaniline → 2-Fluoro-5-(3-fluorophenyl)-N-(3-methoxyphenyl)benzamide

HRID 1771587
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1771587
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].C([O-])([O-])=O.[K+].[K+]>O=S(Cl)Cl.C1COCC1>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([NH:23][C:22]1[CH:24]=[CH:25][CH:26]=[C:20]([O:19][CH3:18])[CH:21]=1)=[O:6]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 108243-MethoxyanilineHCID 11430Potassium CarbonateHCID 463123323',4-Difluoro-[1,1'-biphenyl]-3-carboxylic acid

Produkt 1

HCID 894442352-Fluoro-5-(3-fluorophenyl)-N-(3-methoxyphenyl)benzamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel
HCID 24386
Thionyl Chloride
Lösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 2-fluoro-5-(3-fluorophenyl)benzoic acid (intermediate III(a)) (500 mg, 2.10 mmol, 1.0 eq) in SOCl2 (5 mL) was heated at 65° C. under N2 for 1 h. The solution was then evaporated in vacuo and the remaining residue dissolved in CH2Cl2 and added dropwise to a mixture of 3-methoxyaniline (220 mg. 1.9 mmol, 0.9 eq) and K2CO3 (1.4 g, 10.1 mmol, 5.0 eq) in THF (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with water and the solution extracted with EtOAc. The combined organic extracts were washed with aqueous Na2CO3 and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a colourless oil (580 mg, 96%).

Aufarbeitung

  1. customThe solution was then evaporated in vacuo
  2. dissolutionthe remaining residue dissolved in CH2Cl2
  3. temperatureto warm to room temperature
  4. customThe reaction was quenched with water
  5. extractionthe solution extracted with EtOAc
  6. washThe combined organic extracts were washed with aqueous Na2CO3 and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-57a0bea7f3b64da4a7bba7e85935a1bf
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09249085B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion