Benzyl Alcohol → 5-benzyloxy-N-methyl-2-nitroaniline

HRID 1430400Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1430400
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.F[C:23]1[CH:24]=[CH:25][C:26]([N+:31]([O-:33])=[O:32])=[C:27]([CH:30]=1)[NH:28][CH3:29]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([O:8][C:23]1[CH:24]=[CH:25][C:26]([N+:31]([O-:33])=[O:32])=[C:27]([CH:30]=1)[NH:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 244Benzyl AlcoholHCID 1140TolueneHCID 11430Potassium CarbonateHCID 229057745-fluoro-N-methyl-2-nitroaniline

Produkt 1

HCID 679540515-benzyloxy-N-methyl-2-nitroanilineAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Benzyl alcohol (49.6 mL, 0.48 mol), tetrabutyl ammonium chloride (6.66 g, 24.0 mmol) and potassium carbonate (40.0 g, 0.29 mol) were added to a toluene solution (200 mL) of 5-fluoro-N-methyl-2-nitroaniline (40.8 g, 0.24 mol), and the mixture was heated under reflux for 3.5 hours. The reaction solution was cooled, and 100 mL of water was added thereto. Thereafter, the mixture was stirred for 1 hour at 60 to 70° C. After the mixture was stirred under ice cooling for 30 minutes, precipitated crystals were collected by filtration. The resulting crystals were washed with water, and dried at 50° C., thereby obtaining 57.1 g of an orange, powdery target compound (yield: 92%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3.5 hours
  3. temperatureThe reaction solution was cooled
  4. stirringAfter the mixture was stirred under ice cooling for 30 minutes
  5. customprecipitated crystals
  6. filtrationwere collected by filtration
  7. washThe resulting crystals were washed with water
  8. customdried at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-5b196df8704a4b269a2393375eb08724
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940889B2

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