4-Bromobenzyl bromide → 1-(4-Bromo-benzyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine

HRID 410332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 410332
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[NH:12][C:11]2=[NH:19])=[CH:4][CH:3]=1.[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1>CC(=O)CC>[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([CH2:9][CH2:8][CH2:7][O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:21][CH:20]=3)[C:11]2=[NH:19])=[CH:25][CH:24]=1

Komponenten

4

Edukt 2

HCID 685274-Bromobenzyl bromideHCID 178509078HCID 178509078, Verbindung

Produkt 1

HCID 462409921-(4-Bromo-benzyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamineAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 1-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (0.40 g, 1.40 mmol) in 2-butanone (30 ml) was added 4-bromobenzyl bromide (0.52 g, 2.1 mmol). The reaction was heated to 90° C. for 16 h. After this time, the resulting suspension was cooled to rt and filtered. The collected solid was washed with additional 2-butanone and then the solid was partitioned between dichloromethane and a saturated solution of NaHCO3. The biphasic mixture was stirred at rt for 10 min and then the organic layer was separated. The aqueous phase was extracted with additional dichloromethane and the combined organic fractions were washed with H2O, dried (Na2SO4), filtered and concentrated under reduced pressure to provide 1-(4-bromo-benzyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine as a white solid (0.532 g, 83%). HPLC-MS 454, 456 [M+1]+.

Aufarbeitung

  1. temperatureAfter this time, the resulting suspension was cooled to rt
  2. filtrationfiltered
  3. washThe collected solid was washed with additional 2-butanone
  4. customthe solid was partitioned between dichloromethane
  5. customthe organic layer was separated
  6. extractionThe aqueous phase was extracted with additional dichloromethane
  7. washthe combined organic fractions were washed with H2O
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-84e7187ae7664f348bcdf5e6667a0c13
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759520B2

Notizen zur Reaktion

Wird geladen…