3,4-Dichloroaniline → HCID 12862635, Verbindung

HRID 65735

Reaktionsgleichung

Reaktionsgleichung von HRID 65735
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[CH:10]12[O:15][CH:11]1[CH2:12][CH2:13][CH2:14]2>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH:5][C@@H:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[OH:15]

Komponenten

3

Edukt 2

HCID 72573,4-DichloroanilineHCID 92446-Oxabicyclo[3.1.0]hexane

Produkt 1

HCID 12862635HCID 12862635, VerbindungAusbeute 44 %

Versuchsvorschrift

A solution of 50.0 g. (0.31 mole) of 3,4-dichloroaniline in 100 ml. of cyclopentene oxide is refluxed for 7 days. The solution is evaporated and the residue triturated with 250 ml. of petroleum ether (b.p. 30°-60° C.) five times to remove unreacted 3,4-dichloroaniline. The residue is treated with excess ethereal hydrogen chloride and the resulting crude hydrochloride salt is recrystallized twice from a methanol/ethyl ether mixture to give trans-2-(3,4-dichloroanilino)cyclopentanol, 38.7 g. (44% yield), m.p. 167°-168° C. The ultraviolet, infrared and nuclear magnetic resonance spectra are consistent with the structure of this product.

Aufarbeitung

  1. customThe solution is evaporated
  2. customthe residue triturated with 250 ml
  3. customof petroleum ether (b.p. 30°-60° C.) five times to remove unreacted 3,4-dichloroaniline
  4. additionThe residue is treated with excess ethereal hydrogen chloride
  5. customthe resulting crude hydrochloride salt is recrystallized twice from a methanol/ethyl ether mixture

Quellen und Nachweise

ORD-Eintrag
ord-427cf403d6b24e01bf077ce29d85e3cb
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04128663

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