4-Bromoaniline → Pentanamide, N-(4-bromophenyl)-5-chloro-

HRID 2288788

Reaktionsgleichung

Reaktionsgleichung von HRID 2288788
S(Cl)(Cl)=O.[Cl:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O.[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.ClCCl>[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][Cl:5])=[CH:16][CH:15]=1

Komponenten

7

Edukt 4

HCID 78074-BromoanilineHCID 8471TriethylamineHCID 142445-Chlorovaleric acidHCID 24386Thionyl Chloride

Produkt 1

HCID 532168Pentanamide, N-(4-bromophenyl)-5-chloro-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

366 mmol (26.7 ml) of thionyl chloride are added dropwise to 183 mmol (25 g) of 5-chlorovaleric acid in 250 ml of toluene heated at reflux. The mixture is stirred at reflux until the evolution of gas has ceased and is then cooled. The solvent is evaporated off. The product obtained is then redissolved in 250 ml of dichloromethane and the temperature is lowered to 5° C. A solution of 183 mmol (31.5 g) of 4-bromoaniline in 100 ml of dichloromethane and 183 mmol (25.5 ml) of triethylamine are added in succession. The reaction mixture is stirred for 4 hours at 5° C. and then for 15 hours at room temperature. Hydrolysis, washing the organic phase with a 1N hydrochloric acid solution and evaporating off the solvents yields the expected product, which is used without being purified.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureat reflux until the evolution of gas
  4. temperatureis then cooled
  5. customThe solvent is evaporated off
  6. customThe product obtained
  7. customis lowered to 5° C
  8. stirringThe reaction mixture is stirred for 4 hours at 5° C.
  9. customHydrolysis
  10. washwashing the organic phase with a 1N hydrochloric acid solution
  11. customevaporating off the solvents

Quellen und Nachweise

ORD-Eintrag
ord-658379e067c0421cbd210af27d6f212f
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06090837

Verknüpfte Notizen

Wird geladen…