Hydrochloric Acid → 4-(4-(2-(4-(1-Naphthyl)piperazinyl)ethyl)phenyl)-2-aminothiazole

HRID 329393

Reaktionsgleichung

Reaktionsgleichung von HRID 329393
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.[C:17]1([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl>C(OCC)(=O)C.CO.CCOCC.C(O)C>[C:17]1([N:27]2[CH2:32][CH2:31][N:30]([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)[CH2:29][CH2:28]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Komponenten

10

Edukt 6

HCID 313Hydrochloric AcidHCID 13421-(1-Naphthyl)piperazineHCID 5238Sodium IodideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 147269834-(2-Chloroethyl)phenyl-2-aminothiazole hydrobromide

Produkt 1

HCID 147269924-(4-(2-(4-(1-Naphthyl)piperazinyl)ethyl)phenyl)-2-aminothiazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 3.19 g (10 mmol) of 4-(4-(2-chloroethyl)phenyl)-2-aminothiazole hydrobromide, 2.12 g (10 mmol) of N-(1-naphthyl)piperazine, 2.79 ml (20 mmol) of triethylamine, 1.06 g (10 mmol) of sodium carbonate, 2 mg of sodium iodide, and 25 ml of ethanol. The reaction was heated at reflux for 5 days, cooled, and the precipitate filtered, and washed with ethanol and water. The orange solid was chromatographed on silica gel using ethyl acetate/methylene chloride as eluent to give a white solid. 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, 1.61 g (31%), 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 5 days
  4. temperaturecooled
  5. filtrationthe precipitate filtered
  6. washwashed with ethanol and water
  7. customThe orange solid was chromatographed on silica gel
  8. customto give a white solid
  9. filtrationthe precipitate filtered
  10. washwashed with ether
  11. customdried
  12. customto give a white solid, 1.61 g (31%), m.p. 274°-277° C.

Quellen und Nachweise

ORD-Eintrag
ord-6a3a57f9eff3466ca564a9e901b59cec
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04891375

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