Benzyl Bromide → 5-(3,4-Dimethoxyphenyl)-2-benzylpyrazolin-3-one

HRID 1078354

Reaktionsgleichung

Reaktionsgleichung von HRID 1078354
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[NH:15][NH:14][C:13](=[O:16])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].N1[C:22]([CH3:23])=[CH:21][C:20](C)=[CH:19][C:18]=1[CH3:25].C(Br)C1C=CC=CC=1>C1(C)C=CC=CC=1.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[NH:15][N:14]([CH2:25][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:13](=[O:16])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 79532,4,6-TrimethylpyridineHCID 220460885-(3,4-Dimethoxyphenyl)-pyrazolin-3-one

Produkt 1

HCID 229023385-(3,4-Dimethoxyphenyl)-2-benzylpyrazolin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5 g of 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one, prepared according to Example 1C, were suspended in 100 ml of toluene. First 3 ml of collidine and subsequently 3.6 ml of benzyl bromide were added dropwise to the suspension. After heating for 6 hours under reflux, the reaction mixture was cooled, and the precipitated crystals were filtered out and washed with isopropanol. The crystals obtained were dissolved in dichloromethane and washed with 2M citric acid. The organic phase was dried with magnesium sulfate and concentrated. For purification the residue was recrystallized from isopropanol. 4 g of 5-(3,4-dimethoxyphenyl)-2-benzyl-pyrazolin-3-one were obtained having a melting point of 165° C.

Aufarbeitung

  1. temperatureAfter heating for 6 hours
  2. temperatureunder reflux
  3. temperaturethe reaction mixture was cooled
  4. filtrationthe precipitated crystals were filtered out
  5. washwashed with isopropanol
  6. customThe crystals obtained
  7. washwashed with 2M citric acid
  8. dry with materialThe organic phase was dried with magnesium sulfate
  9. concentrationconcentrated
  10. customFor purification the residue
  11. customwas recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-eb40e8b17603436787bcc9fe9812463a
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05547967

Verknüpfte Notizen

Wird geladen…