4-Aminobenzaldehyde → 2-(4-Amino-benzylidene)-6-isopropyl-3-methyl-cyclohexanone

HRID 1644242

Reaktionsgleichung

Reaktionsgleichung von HRID 1644242
[CH:1]([CH:4]1[C:9](=[O:10])[C:8](=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]=CC3C=CC(OCCC)=CC=3)=[CH:14][CH:13]=2)[CH:7]([CH3:30])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C[C@H]1CC(=O)[C@H](C(C)C)CC1.NC1C=CC(C=O)=CC=1.[OH-].[K+]>CS(C)=O.O.C(OCC)(=O)C>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([CH:11]=[C:8]2[CH:7]([CH3:30])[CH2:6][CH2:5][CH:4]([CH:1]([CH3:2])[CH3:3])[C:9]2=[O:10])=[CH:17][CH:16]=1

Komponenten

8

Edukt 4

HCID 111584-AminobenzaldehydeHCID 14797Potassium HydroxideHCID 26447MenthoneHCID 28510996-Isopropyl-3-methyl-2-{4-[(4-propoxy-benzylidene)-amino]-benzylidene}-cyclohexanone3×

Produkt 1

HCID 50230232-(4-Amino-benzylidene)-6-isopropyl-3-methyl-cyclohexanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A compound having general Formula 3, exemplified by 6-Isopropyl-3-methyl-2-{4-[(4-propoxy-benzylidene)-amino]-benzylidene}-cyclohexanone (Compound 3; FIG. 1) can be prepared as follows. A solution of menthone (154 mg, 1.0 mmol) and 4-aminobenzaldehyde (121 mg, 1.0 mmol) in dimethylsulfoxide is treated with potassium hydroxide (56 mg, 1.0 mmol). The reaction is stirred until no futher reaction occurs. The reaction mixture is poured into ethyl acetate and water. The organic phase is collected, dried and concentrated to give 2-(4-Amino-benzylidene)-6-isopropyl-3-methyl-cyclohexanone. The 2-(4-Amino-benzylidene)-6-isopropyl-3-methyl-cyclohexanone is dissolved in dichloromethane and treated with 4-propoxybenzaldehyde (164 mg, 1.0 mmol) and anhydrous Na2SO4. The reaction mixture is stirred until no further reaction occurs. The reaction mixture is filtered and concentrated to give the title compound.

Aufarbeitung

  1. customcan be prepared
  2. customThe organic phase is collected
  3. customdried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4327ab900b4741d1acdb5fffdaf9feb5
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124612B2

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