Bromine → HCID 86644708, Verbindung

HRID 455242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455242
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([F:27])=[C:11]([NH:13][C:14](=[O:26])[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[CH:12]=2)=[C:4]([C:30]#[N:31])[CH:3]=1.[S-:32][C:33]#[N:34].[K+].BrBr>C(O)(=O)C>[NH2:34][C:33]1[S:32][C:3]2[C:4]([C:30]#[N:31])=[C:5]([O:6][C:7]3[CH:8]=[CH:9][C:10]([F:27])=[C:11]([NH:13][C:14](=[O:26])[CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=4)[CH:12]=3)[CH:28]=[CH:29][C:2]=2[N:1]=1

Komponenten

5

Edukt 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 66810488HCID 66810488, Verbindung

Produkt 1

HCID 86644708HCID 86644708, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel3×

Versuchsvorschrift

To a solution of N-[5-(4-amino-2-cyanophenoxy)-2-fluorophenyl]-2-[3-(trifluoromethyl)phenyl]acetamide (1.15 g, 2.68 mmol) in acetic acid (40 mL) was added potassium thiocyanate (1.22 g, 12.6 mmol), and the mixture was stirred at room temperature for 10 min. A solution of bromine (652 mg, 4.08 mmol) in acetic acid (6.5 mL) was added dropwise to the obtained solution over 10 min. After the completion of the dropwise addition, the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with acetic acid (50 mL), and insoluble material was filtered off and washed with acetic acid, the filtrate and washings were combined and the mixture was concentrated under reduced pressure. The obtained residue was suspended in ethyl acetate (120 mL)/tetrahydrofuran (12 mL), and the suspension was washed successively with saturated aqueous sodium hydrogen carbonate solution (120 mL) and saturated brine (120 mL), and dried over anhydrous magnesium sulfate. Insoluble material was filtered off, the filtrate was purified by basic silica gel column chromatography (eluate: ethyl acetate), and the obtained solution was concentrated under reduced pressure to give the title compound (1.13 g, 87%) as a beige powder.

Aufarbeitung

  1. additionAfter the completion of the dropwise addition
  2. stirringthe mixture was stirred at room temperature for 12 hr
  3. filtrationwas filtered off
  4. washwashed with acetic acid
  5. concentrationthe mixture was concentrated under reduced pressure
  6. washthe suspension was washed successively with saturated aqueous sodium hydrogen carbonate solution (120 mL) and saturated brine (120 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationInsoluble material was filtered off
  9. customthe filtrate was purified by basic silica gel column chromatography (eluate: ethyl acetate)
  10. concentrationthe obtained solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-78c255aca1184f69a2c31dc91678f435
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497274B2

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