N-(3,4-Dichlorophenyl)thiourea → 6-((2-(3,4-dichlorophenylamino)thiazol-4-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1023181

Reaktionsgleichung

Reaktionsgleichung von HRID 1023181
Br[CH2:2][C:3](=O)[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2.[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27]([NH2:29])=[S:28])[CH:22]=[CH:23][C:24]=1[Cl:25]>C(O)C>[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27]2[S:28][CH:2]=[C:3]([CH2:4][O:5][C:6]3[CH:7]=[C:8]4[C:13](=[CH:14][CH:15]=3)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]4)[N:29]=2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Komponenten

4

Edukt 2

HCID 710776N-(3,4-Dichlorophenyl)thioureaHCID 866804256-(3-bromo-2-oxopropoxy)-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 715420416-((2-(3,4-dichlorophenylamino)thiazol-4-yl)methoxy)-3,4-dihydroquinolin-2(1H)-oneAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-(3-bromo-2-oxopropoxy)-3,4-dihydroquinolin-2(1H)-one (0.15 g, 0.503 mmol) in ethanol (3 mL) was added 1-(3,4-dichlorophenyl)thiourea (0.133 g, 0.604 mmol). The reaction mixture was refluxed for 12 h, then concentrated and purified by preparative HPLC to afford a white solid (0.05 g, 24%). 1H NMR 400 MHz, DMSO-d6: δ 2.40 (t, J=7.20 Hz, 2H), 2.85 (t, J=8.00 Hz, 2H), 4.99 (s, 2H), 6.80 (d, J=8.80 Hz, 1H), 6.87 (q, J=2.80 Hz, 1H), 6.92 (d, J=2.40 Hz, 1H), 6.98 (s, 1H), 7.48-7.49 (m, 2H), 8.06 (d, J=2.00 Hz, 1H), 9.92 (s, 1H), 10.56 (s, 1H). LCMS: RT 1.99 min; LCMS (ES-API), m/z 420. LCMS: RT 1.99 min; LCMS (ES-API), m/z 420.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 12 h
  2. concentrationconcentrated
  3. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-fa80333a63c44c39a55fd6c2daedc10c
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722670B2

Verknüpfte Notizen

Wird geladen…