Sodium hydride → 2-[4-(4-Chlorophenyl)-1-piperazinyl]-ethyl 3-(8-trifluoromethyl 4-quinolylamino)-2-thiophene-carboxylate

HRID 838948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 838948
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[NH:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]([O:21][CH3:22])=[O:20].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][N:35]([CH2:38]CO)[CH2:34][CH2:33]2)=[CH:28][CH:27]=1.[H-].[Na+]>C1(C)C=CC=CC=1>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[NH:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]([O:21][CH2:22][CH2:38][N:35]1[CH2:34][CH2:33][N:32]([C:29]2[CH:30]=[CH:31][C:26]([Cl:25])=[CH:27][CH:28]=2)[CH2:37][CH2:36]1)=[O:20]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2582112-[4-(4-Chlorophenyl)piperazin-1-yl]ethanolHCID 15916787Methyl 3-(8-trifluoromethyl-4-quinolylamino)-2-thiophene-carboxylate

Produkt 1

HCID 203254662-[4-(4-Chlorophenyl)-1-piperazinyl]-ethyl 3-(8-trifluoromethyl 4-quinolylamino)-2-thiophene-carboxylateAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 7.04 g of methyl 3-(8-trifluoromethyl-4-quinolylamino)-2-thiophene-carboxylate, 5.5 g of 4-(4-chlorophenyl)-1-piperazine ethanol and 50 ml of anhydrous toluene was refluxed for an hour while passing condensed toluene through a column filled with siliporite and after cooling the mixture to 60° C, 150 ml of sodium hydride were added. The mixture was refluxed with stirring for 16 hours and the toluene was distilled. The residue was extracted with methylene chloride, was washed and dried. The product was crystallized from 95% ethanol, iced and vacuum filtered. The precipitate was washed with ethanol and dried to obtain 8.6 g of 2-[4-(4-chlorophenyl)-1-piperazinyl]-ethyl 3-(8-trifluoromethyl 4-quinolylamino)-2-thiophene-carboxylate melting at 155° C.

Aufarbeitung

  1. temperaturewas refluxed for an hour
  2. additionfilled with siliporite and
  3. temperatureThe mixture was refluxed
  4. distillationthe toluene was distilled
  5. extractionThe residue was extracted with methylene chloride
  6. washwas washed
  7. customdried
  8. customThe product was crystallized from 95% ethanol
  9. filtrationiced and vacuum filtered
  10. washThe precipitate was washed with ethanol
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-cdb6d4f942434e97a4b5e05c05f13702
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093724

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