HCID 13768101, Verbindung → N-diethylphosphoryl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide

HRID 1789355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789355
[CH2:1]([P:3]([N:7]=[C:8]=[S:9])([CH2:5][CH3:6])=[O:4])[CH3:2].[F:10][C:11]1[CH:12]=[C:13]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH:32]3[NH:36][CH2:35][CH2:34][S:33]3)[CH2:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1>CC(C)=O>[CH2:1]([P:3]([NH:7][C:8]([N:36]1[CH2:35][CH2:34][S:33][CH:32]1[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[O:25][CH2:24][CH2:23][N:20]1[CH2:19][CH2:18][N:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([F:10])[CH:12]=2)[CH2:22][CH2:21]1)=[S:9])([CH2:5][CH3:6])=[O:4])[CH3:2]

Komponenten

4

Edukt 2

HCID 13768101HCID 13768101, VerbindungHCID 20188170Diethylphosphoryl isothiocyanate

Produkt 1

HCID 14095401N-diethylphosphoryl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamideAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

0.68 g of diethylphosphoryl isothiocyanate is added to a solution of 1.23 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine in 20 ml of acetone, and the mixture is stirred for one day. The mixture is concentrated under reduced pressure to remove solvent. The residue is extracted with chloroform, and the extract is washed with a saturated sodium chloride solution, dried and concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, chloroform:methanol=40:1), and the resultant product is recrystallized from ethyl acetate and ether. 1.49 g of N-diethylphosphoryl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide are obtained. Yield: 81%.

Aufarbeitung

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customto remove solvent
  3. extractionThe residue is extracted with chloroform
  4. washthe extract is washed with a saturated sodium chloride solution
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto remove solvent
  8. customThe residue is purified by silica gel chromatography (solvent, chloroform:methanol=40:1)
  9. customthe resultant product is recrystallized from ethyl acetate and ether

Quellen und Nachweise

ORD-Eintrag
ord-1bfbce77124b4ef7b75e6c9cc7cb718a
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04689327

Notizen zur Reaktion

Wird geladen…