Stannous chloride dihydrate → 4-(4-Cyclohexylphenoxy)-2,5-dimethylaniline

HRID 405004

Reaktionsgleichung

Reaktionsgleichung von HRID 405004
[CH:1]1([C:7]2[CH:24]=[CH:23][C:10]([O:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([N+:19]([O-])=O)=[C:14]([CH3:22])[CH:13]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.Cl>[CH:1]1([C:7]2[CH:24]=[CH:23][C:10]([O:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([NH2:19])=[C:14]([CH3:22])[CH:13]=3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

6

Edukt 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 685962084-(4-Cyclohexylphenoxy)-2,5-dimethylnitrobenzene

Produkt 1

HCID 685960764-(4-Cyclohexylphenoxy)-2,5-dimethylanilineAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 0.49 g (1.5 mmol) of 4-(4-cyclohexylphenoxy)-2,5-dimethylnitrobenzene in 7 ml of dioxane and 7 ml of hydrochloric acid is admixed with 1.01 g (4.5 mmol) of tin(II) chloride dihydrate at room temperature and the mixture is then refluxed for 2 h. It is cooled to room temperature, neutralized with aqueous NaHCO3 and extracted repeatedly with dichloromethane, and the extracts are dried over Na2SO4 and filtered, and the solvent is removed under reduced pressure. This is followed by purification by column chromatography (0.29 g, purity 95.2%, yield 61.5%, log P (pH 2.3)=4.25).

Aufarbeitung

  1. temperaturethe mixture is then refluxed for 2 h
  2. extractionextracted repeatedly with dichloromethane
  3. dry with materialthe extracts are dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent is removed under reduced pressure
  6. customThis is followed by purification by column chromatography (0.29 g, purity 95.2%, yield 61.5%, log P (pH 2.3)=4.25)

Quellen und Nachweise

ORD-Eintrag
ord-018238e3bc1740f199fda69cbcf3f27c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748662B2

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