Toluene → N-benzyl-4-methylaniline

HRID 382091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 382091
CC([O-])(C)C.[Na+].[C:7]1([CH3:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.ClC1C=CC(C)=CC=1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:22]([NH:29][C:10]1[CH:11]=[CH:12][C:7]([CH3:13])=[CH:8][CH:9]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 7504BenzylamineHCID 78104-ChlorotolueneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 79403N-benzyl-4-methylanilineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

An oven dried resealable Schlenk tube was purged with argon and charged with Pd2(dba)3 (4.6 mg, 0.005 mmol, 1.0 mol % Pd), 27 (7.4 mg, 0.015 mmol, 1.5 mol %), and NaOtBu (135 mg, 1.4 mmol). The tube was purged with argon and toluene (2 mL), 4-chlorotoluene (0.12 mL, 1.0 mmol), and benzylamine (0.165 mL, 1.5 mmol) were added through a rubber septum. The septum was replaced with a teflon screw cap, the tube was sealed, and the mixture was heated to 100° C. with stirring until the starting aryl chloride had been completely consumed as judged by GC analysis. A small amount of diarylated benzylamine was detected in the crude reaction mixture (GC ratio of product/diarylated benzylamine=16/1). The reaction mixture was cooled to room temperature, diluted with ether (20 mL), and extracted with 1 M HCl (5×40 mL). The organic phase was discarded and the combined aqueous extracts were basisified to pH 14 with 6M NaOH and extracted with ether (4×50 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give give 175 mg (89%) of a pale yellow oil.

Aufarbeitung

  1. customAn oven dried resealable Schlenk tube
  2. customwas purged with argon
  3. additionwere added through a rubber septum
  4. customscrew cap
  5. customthe tube was sealed
  6. customhad been completely consumed
  7. customreaction mixture (GC ratio of product/diarylated benzylamine=16/1)
  8. temperatureThe reaction mixture was cooled to room temperature
  9. extractionextracted with 1 M HCl (5×40 mL)
  10. extractionextracted with ether (4×50 mL)
  11. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customto give

Quellen und Nachweise

ORD-Eintrag
ord-cee495c931444601ac1f909a553d8573
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307087B1

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