1,2-Dichloroethane → HCID 178506207, Verbindung

HRID 491656

Reaktionsgleichung

Reaktionsgleichung von HRID 491656
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([O:11][C:12]2[CH:13]=[C:14]([NH2:19])[C:15]([NH2:18])=[CH:16][CH:17]=2)=[CH:3][CH:2]=1.[N:20]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)=[C:21]=S.C(Cl)CCl>CC#N>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([O:11][C:12]2[CH:17]=[CH:16][C:15]3[NH:18][C:21]([NH:20][C:23]4[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=4)=[N:19][C:14]=3[CH:13]=2)=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 111,2-DichloroethaneHCID 1371344-(Trifluoromethyl)phenyl isothiocyanateHCID 177564934-(Quinolin-4-yloxy)-benzene-1,2-diamine

Produkt 1

HCID 178506207HCID 178506207, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel3×

Versuchsvorschrift

To a solution of 4-(quinolin-4-yloxy)-benzene-1,2-diamine (Step B, 227 mg) in CH3CN (60 mL) was added over 5 min, a solution of 1-isothiocyanato-4-trifluoromethyl-benzene (183 mg) in CH3CN 10 mL). The mixture was stirred for 12 h at RT and EDC (260 mg) was added, followed by CH3CN (30 mL). The resulting mixture was heated at 80° C. for 2 h, then cooled to RT. The solvent was evaporated and the residue was dissolved in EtOAc and washed with water. The organic phase was dried, filtered and evaporated. The residue was purified by flash chromatography in EtOAc to give an orange-brown solid. MS (MH+)=420.9, MW: 420.18 Calc'd for: C23H15F3N4O.

Aufarbeitung

  1. temperatureThe resulting mixture was heated at 80° C. for 2 h
  2. temperaturecooled to RT
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with water
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography in EtOAc
  10. customto give an orange-brown solid

Quellen und Nachweise

ORD-Eintrag
ord-e55ed9548e514eb1bda4beff656cd96e
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531553B2

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