Benzydamine Hydrochloride → 4-(2-Hydroxyphenyl)-2-phenyl-pyrimidine

HRID 1977608

Reaktionsgleichung

Reaktionsgleichung von HRID 1977608
Br[CH:2]1C(=O)C2C(=CC=CC=2)[O:4][CH2:3]1.CN(CCCO[C:20]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=2[N:27]([CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:28]=1)C.Cl.C1CCN2C(=NCCC2)CC1>C(O)C>[OH:4][C:3]1[CH:2]=[CH:22][CH:23]=[CH:24][C:25]=1[C:26]1[CH:21]=[CH:20][N:28]=[C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:27]=1

Komponenten

5

Edukt 3

HCID 65464Benzydamine HydrochlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123873063-Bromochroman-4-one

Produkt 1

HCID 1355464764-(2-Hydroxyphenyl)-2-phenyl-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-bromo-chroman-4-one (2.5 g) and benzydamine hydrochloride (1.7 g) in dry ethanol (25 ml) was refluxed for 6 hours in the presence of DBU (1.7 g). The reaction mixture was cooled, then evaporated to dryness and the residue was partitioned between ethyl acetate and a diluted hydrochloric acid aqueous solution. The organic layer was washed with a diluted sodium carbonate aqueous solution, with water, dried and evaporated to dryness to give the crude title compound. This was purified through its hydrochloride, prepared by dissolving the free base in acetone and adding an HCI ethereal solution.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customevaporated to dryness
  3. customthe residue was partitioned between ethyl acetate
  4. washThe organic layer was washed with a diluted sodium carbonate aqueous solution, with water
  5. customdried
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-062f9be89e9444ef8bbd630e97a74156
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235738B1

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