Pyridine → N-(2-bromophenethyl)-4-(trifluoromethyl)benzamide

HRID 445367

Reaktionsgleichung

Reaktionsgleichung von HRID 445367
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH2:6].N1C=CC=CC=1.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH:6][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][C:19]([C:18]([F:17])([F:28])[F:29])=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 27340912-Bromophenethylamine

Produkt 1

HCID 59536435N-(2-bromophenethyl)-4-(trifluoromethyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a 100 mL round-bottomed flask was added 2-bromophenethylamine (1800 mg, 9 mmol, Aldrich), pyridine (5 mL), 4-(trifluoromethyl)benzoyl chloride (2 mL, 9 mmol, Fluka). The reaction mixture was stirred at RT for 1 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The organic extract was washed with water (30 mL), saturated NaCl (30 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 30% EtOAc/hexanes to give N-(2-bromophenethyl)-4-(trifluoromethyl)benzamide. MS (ESI pos. ion) m/z: 372 (M+1).

Aufarbeitung

  1. extractionextracted with EtOAc (2×50 mL)
  2. extractionThe organic extract
  3. washwas washed with water (30 mL), saturated NaCl (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 30% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-27fbe7920714473daa9f13cce5a20c11
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476297B2

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