Hydrochloric Acid → HCID 86658249, Verbindung
Reaktionsgleichung
Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[C:7]([NH:9][CH2:10][C:11]([F:14])([F:13])[F:12])[CH:8]=1.Cl[C:17]1[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=1.O>CS(C)=O>[Br:2][C:3]1[CH:4]=[C:5]([NH:15][C:17]2[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=2)[CH:6]=[C:7]([NH:9][CH2:10][C:11]([F:13])([F:14])[F:12])[CH:8]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
Aqueous HCl (1.0 M, 1.5 mL, 1.5 mmol) was added to a stirred mixture of the product of Step 2 (0.80 g, 2.97 mmol) and 2-chloro-4-trifluoromethylpyrimidine (8.0 mL, 66.2 mmol) in DMSO and the mixture was stirred at 100° C. for 2 h. The mixture was cooled, water was added and the mixture was extracted with Et2O (3×). The combined organic fractions were washed with HCl, water, aqueous copper sulfate and brine, dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (0-60% ethyl acetate in hexanes) to give 5-bromo-N-(2,2,2-trifluoroethyl)-N′-[4-(trifluoromethyl)-pyrimidin-2-yl]benzene-1,3-diamine (622 mg, 1.50 mmol, 50% yield) as a off-white solid. MS ESI: [M+H]+ m/z 416.9.
Aufarbeitung
- temperatureThe mixture was cooled
- extractionthe mixture was extracted with Et2O (3×)
- washThe combined organic fractions were washed with HCl, water, aqueous copper sulfate and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by column chromatography (0-60% ethyl acetate in hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-98d7e2a5ecf54386be9f3abc1d5cc38a
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08759366B2
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