Triethylamine → 4-(4-(2-(4-(3-Trifluoromethylphenyl)piperazinyl)ethyl)phenyl)thiazol-2-one

HRID 329398

Reaktionsgleichung

Reaktionsgleichung von HRID 329398
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12](=[O:15])[S:13][CH:14]=2)=[CH:6][CH:5]=1.Cl.[F:17][C:18]([F:32])([F:31])[C:19]1[CH:20]=[C:21]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[Na+].CC(CC(C)C)=O>[F:32][C:18]([F:17])([F:31])[C:19]1[CH:20]=[C:21]([N:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([C:10]4[NH:11][C:12](=[O:15])[S:13][CH:14]=4)=[CH:6][CH:5]=3)[CH2:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 3084246TFMPP hydrochlorideHCID 150542144-(4-(2-Chloroethyl)phenyl)thiazol-2-one

Produkt 1

HCID 198720674-(4-(2-(4-(3-Trifluoromethylphenyl)piperazinyl)ethyl)phenyl)thiazol-2-oneAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5238Sodium IodideKatalysatorHCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.89 g (7.89 mmol) of 4-(4-(2-chloroethyl)phenyl)thiazol-2-one, 2.10 g (7.89 mmol) of N-(3-trifluoromethylphenyl)piperazine hydrochloride, 2.20 ml (15.8 mmol) of triethylamine, 0.84 g (7.89 mmol) of sodium carbonate, 2 mg of sodium iodide, and 20 ml of methylisobutylketone. The reaction was heated at reflux for 6 days, cooled, and evaporated. The residue was taken up in ethyl acetate/water, the layers separated, and the ethyl acetate layer washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using ethyl acetate/methylene chloride as eluent. The product fractions were evaporated, and the residue triturated with ether, taken up in hot ethyl acetate, treated with ethyl acetate saturated with hydrochloride, precipitated with ether, filtered, washed with ether, and dried to give 0.787 g (20%) of a white solid, m.p. 285°-287° C.

Aufarbeitung

  1. customTo a 35 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 6 days
  4. temperaturecooled
  5. customevaporated
  6. customthe layers separated
  7. washthe ethyl acetate layer washed with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customThe residue was chromatographed on silica gel
  11. customThe product fractions were evaporated
  12. customthe residue triturated with ether
  13. additiontreated with ethyl acetate saturated with hydrochloride
  14. customprecipitated with ether
  15. filtrationfiltered
  16. washwashed with ether
  17. customdried

Quellen und Nachweise

ORD-Eintrag
ord-865637f215114543badab6e375b70dcb
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04891375

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