Sodium Iodide → 4-(4-(2-(4-(3-Trifluoromethylphenyl)piperazinyl)ethyl)phenyl)-2-aminothiazole

HRID 329394

Reaktionsgleichung

Reaktionsgleichung von HRID 329394
Br.Cl[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH2:16])[S:14][CH:15]=2)=[CH:7][CH:6]=1.Cl.[F:18][C:19]([F:33])([F:32])[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(O)C>[F:33][C:19]([F:18])([F:32])[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][N:29]([CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][C:8]([C:11]4[N:12]=[C:13]([NH2:16])[S:14][CH:15]=4)=[CH:7][CH:6]=3)[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1

Komponenten

7

Edukt 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 3084246TFMPP hydrochlorideHCID 147269834-(2-Chloroethyl)phenyl-2-aminothiazole hydrobromide

Produkt 1

HCID 142114364-(4-(2-(4-(3-Trifluoromethylphenyl)piperazinyl)ethyl)phenyl)-2-aminothiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 0.81 g (2.55 mmol) of 4-(4-(2-chloroethyl)phenyl)-2-aminothiazole hydrobromide, 0.68 g (2.55 mmol) of N-(3-trifluoromethylphenyl)piperazine hydrochloride, 1.06 ml (7.64 mmol) of triethylamine, 0.27 g (2.55 mmol) of sodium carbonate, 2 mg of sodium iodide, and 10 ml of ethanol. The reaction was heated at reflux for 8 days, cooled, and the precipitate filtered, and the reaction mixture taken up in ethyl acetate/water. The layers were separated, the ethyl acetate washed with brine, dried, and evaporated to give a white solid, which was triturated with ethyl acetate. The solid was taken up in ethyl acetate/methanol, ether saturated with HCl added, the precipitate filtered, washed with ether, and dried to give a white solid, 0.255 g (18%), m.p. 274°-277° 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 8 days
  4. temperaturecooled
  5. filtrationthe precipitate filtered
  6. customThe layers were separated
  7. washthe ethyl acetate washed with brine
  8. customdried
  9. customevaporated
  10. customto give a white solid, which
  11. customwas triturated with ethyl acetate
  12. additionether saturated with HCl added
  13. filtrationthe precipitate filtered
  14. washwashed with ether
  15. customdried
  16. customto give a white solid, 0.255 g (18%), m.p. 274°-277° C.

Quellen und Nachweise

ORD-Eintrag
ord-97602c7bc3e047e2802381429e7e193b
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04891375

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