StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1,2-Dichloroethane → HCID 178503457, Verbindung

HRID 491642
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 491642
[CH3:1][S:2][C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:11]=[C:12]([NH2:17])[C:13]([NH2:16])=[CH:14][CH:15]=2)[CH:6]=[CH:5][N:4]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=S)=[CH:21][C:20]=1[C:28]([F:31])([F:30])[F:29].C(Cl)CCl>CC#N>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]2[NH:16][C:13]3[CH:14]=[CH:15][C:10]([O:9][C:7]4[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=4)=[CH:11][C:12]=3[N:17]=2)=[CH:21][C:20]=1[C:28]([F:29])([F:30])[F:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 111,2-DichloroethaneHCID 5200261-Chloro-4-isothiocyanato-2-(trifluoromethyl)benzeneHCID 177564954-(2-Methylsulfanyl-pyrimidin-4-yloxy)-benzene-1,2-diamine

Produkt 1

HCID 178503457HCID 178503457, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 4-(2-methylsulfanyl-pyrimidin-4-yloxy)-benzene-1,2-diamine (Example 18, Step B, 400 mg, 1.6 mmol, 1.0 eq.) in anhydrous CH3CN (20 mL) was added drop wise a solution of 1-chloro-4-isothiocyanato-2-trifluoromethylbenzene (380 mg, 1.6 mmol, 1.0 eq.) in anhydrous CH3CN (10 mL). The solution was stirred for 16 h at RT. EDC (470 mg, 2.4 mmol, 1.5 eq.) was added and the reaction was heated to 80° C. and stirred for 2 h. The solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2, and the solution was washed with H2O (25 mL), NaHCO3 (aq., 25 mL) and brine (25 mL). The aqueous layers were back extracted with CH2Cl2 and the combined organic layers were dried over MgSO4, filtered and concentrated. The crude was further purified by column chromatography (0-100% EtOAc/hexanes) to yield (4-chloro-3-trifluoromethyl-phenyl)-[5-(2-methylsulfanyl-pyrimidin-4-yloxy)-1H-benzimidazol-2-yl]-amine. MS m/z=452.1 (M+H)+; MW Calc'd for C19H13ClF3N5OS: 451.86.

Aufarbeitung

  1. temperaturethe reaction was heated to 80° C.
  2. stirringstirred for 2 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washthe solution was washed with H2O (25 mL), NaHCO3 (aq., 25 mL) and brine (25 mL)
  6. extractionThe aqueous layers were back extracted with CH2Cl2
  7. dry with materialthe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude was further purified by column chromatography (0-100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-272ac781531741b08f5ebb853b69f3cc
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07531553B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion