Sodium Iodide → N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789347
[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])=[O:4].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:30][CH2:29]1>CN(C)C=O>[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)=[O:4]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 47418781-(2-Chloroethyl)-4-phenylpiperazineHCID 137496082-(2-Hydroxyphenyl)-N-methyl-1,3-thiazolidine-3-carboxamide

Produkt 1

HCID 13767927N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamideAusbeute 44,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2.38 g of N-methyl-2-(2-hydroxyphenyl)thiazolidine-3-carboxamide, 1.38 g of potassium carbonate, 0.7 g of sodium iodide, 3.36 g of 1-(2-chloroethyl)-4-phenylpiperazine and 25 ml of dimethylformamide is stirred at 90° C. for 24 hours. The mixture is concentrated under reduced pressure to remove dimethylformamide. Water is added to the residue, and the aqueous mixture is extacted with ethyl acetate. The extract is washed with dilute sodium hydroxide solution and water, successively. The ethyl acetate solution is dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (sovent, benzene:ethyl acetate-1:5). 1.89 g of N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide are obtained.

Aufarbeitung

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customto remove dimethylformamide
  3. additionWater is added to the residue
  4. washThe extract is washed with dilute sodium hydroxide solution and water
  5. dry with materialThe ethyl acetate solution is dried
  6. concentrationconcentrated under reduced pressure
  7. customto remove solvent
  8. customThe residue is purified by silica gel chromatography (sovent, benzene:ethyl acetate-1:5)

Quellen und Nachweise

ORD-Eintrag
ord-99a2331c88664704a50a163db33a54cd
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04689327

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