Triethylamine → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}-N'-(3-diethylaminopropyl)thiourea

HRID 721462

Reaktionsgleichung

Reaktionsgleichung von HRID 721462
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([CH3:23])[C:17]=1[CH3:24].[CH2:25]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH3:26].[C:32](Cl)(Cl)=[S:33].[CH2:36]([N:38](CC)CC(N)C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:32]([NH:38][CH2:36][CH2:26][CH2:25][N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[S:33])=[C:18]([CH3:23])[C:17]=1[CH3:24]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 16643481(2-Aminopropyl)diethylamineHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

Produkt 1

HCID 21890609N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}-N'-(3-diethylaminopropyl)thioureaAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (51 mg) was dissolved in N,N-dimethylformamide (2 ml) and triethylamine (1 ml) to prepare a solution. Thiophosgene (51 mg) was then added to the solution, and the mixture was stirred at room temperature for 6 hr. Next, N,N-diethylpropylenediamine (50 mg) was added thereto, and the mixture was further stirred at room temperature for 15 hr. Ethyl acetate was added to the reaction solution, followed by washing with water and saturated brine in that order. The organic layer was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by HPLC using chloroform/methanol for development to give the title compound (36 mg, yield 45%).

Aufarbeitung

  1. stirringthe mixture was further stirred at room temperature for 15 hr
  2. washby washing with water and saturated brine in that order
  3. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customthe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f52d6f4111274753834c3f9763d514d6
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135466B2

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