Hydrochloric Acid → HCID 21937664, Verbindung

HRID 1241938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1241938
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[NH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C.Cl>CN(C=O)C>[CH:20]1([CH2:19][NH:18][C:2]2[CH:7]=[CH:6][C:5]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][C:3]=2[N+:15]([O-:17])=[O:16])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 76688CyclohexanemethylamineHCID 81531DiisopropylethylamineHCID 219378011-Chloro-2-nitro-4-phenoxybenzene

Produkt 1

HCID 21937664HCID 21937664, VerbindungAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-chloro-2-nitro-4-phenoxy-benzene (0.60 g, 2.58 mmol), (aminomethyl)cyclohexane (1.0 mL, 7.76 mmol) and N,N′-diisopropylethylamine (1.36, 7.76 mmol) in DMF (20.00 mL) was stirred at 100° C. under an inert atmosphere for 18.5 h. The reaction mixture was transferred to a separatory funnel containing HCl (2.0 N). The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water, brine and dried over MgSO4. The solution was filtered through diatomaceous earth and the solvent was evaporated. The resulting dark red residue was flash chromatographed (10% EtOAc/hexane) to give cyclohexylmethyl-(2-nitro-4-phenoxy-phenyl)-amine as a dark red solid (0.55 g, 65.6% yield).

Aufarbeitung

  1. customThe reaction mixture was transferred to a separatory funnel
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic layers were washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered through diatomaceous earth
  6. customthe solvent was evaporated
  7. customchromatographed (10% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-68d50fd329664e7592593e61bde894de
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115644B2

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