Water → HCID 9847995, Verbindung

HRID 984460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 984460
Cl[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:20])[CH3:19])[CH2:14][CH2:13]2)=[O:11])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].C(=O)([O-])[O-].[K+].[K+].[Cl:30][C:31]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:32]=1[SH:38].O>CN(C=O)C>[Cl:30][C:31]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:32]=1[S:38][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:20])[CH3:19])[CH2:14][CH2:13]2)=[O:11])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 707302,4-DichlorobenzenethiolHCID 10664709(E)-1-(4-acetylpiperazin-1-yl)-3-(4-chloro-3-nitrophenyl)prop-2-en-1-one

Produkt 1

HCID 9847995HCID 9847995, VerbindungAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-chloro-3-nitro-cinnamide (275 mg, 0.814 mmol) from Example 32A in 1.0 mL of DMF was added potassium carbonate (169 mg, 1.22 mmol), followed by the dropwise addition of 2,4-dichlorothiophenol (146 mg, 0.815 mmol). The mixture was then stirred at room temperature for 60 minutes. Completion of the reaction was indicated by the TLC. Water was then added to precipitate the product. Filtration, washing with cold water, and drying in a vacuum oven afforded 350 mg (0.728 mmol, 89%) of the titled compound as a light yellow solid. 1H NMR (d6-DMSO, 300 MHz) δ 2.05 (s, 3H), 3.42-3.50 (br m, 4H), 3.50-3.64 (br m, 2H), 3.64-3.79 (br m, 2H), 6.83 (d, J=8.7 Hz, 1H), 7.44 (d, J=15.3, Hz, 1H), 7.55 (d, J=15.3 Hz, 1H), 7.63 (dd, J=2.7, 8.7 Hz, 1H), 7.83 (d, J=8.7 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.96 (d, J=2.7 Hz, 1H), 8.69 (d, J=1.8 Hz, 1H). MS (DCI/NH3) (M+H)+ at m/z 497, 499, 501. Analysis calculated for C21H19N3O4 Cl2 S1.0.82H2O: C, 50.94; H, 4.20; N, 8.49. Found: C, 50.91; H, 4.21; N, 8.69.

Aufarbeitung

  1. customto precipitate the product
  2. filtrationFiltration
  3. washwashing with cold water
  4. customdrying in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-9266347b234c4f37acb28fe25c5aa770
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867203B2

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