Dichloromethane → 2-(4-Chlorophenyl)imino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-one

HRID 51221

Reaktionsgleichung

Reaktionsgleichung von HRID 51221
[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:6][C:5](=S)[N:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15].C(Cl)Cl.F[B-](F)(F)F.C([O+](CC)CC)C.[Cl:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1>C(Cl)(Cl)Cl.O>[Cl:37][C:38]1[CH:44]=[CH:43][C:41]([N:42]=[C:5]2[N:4]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:3](=[O:15])[C:2]([CH3:1])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:6]2)=[CH:40][CH:39]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 78124-ChloroanilineHCID 2723982Triethyloxonium tetrafluoroborateHCID 120563925-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one

Produkt 1

HCID 120563992-(4-Chlorophenyl)imino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-oneAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

5-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one (0.28 g) was mixed with a 1M methylene chloride solution of triethyloxonium tetrafluoroborate (1 ml) at room temperature. The reaction mixture was stirred for 24 hrs at room temperature then p-chloroaniline (0.25 g) in chloroform (10 ml) was added to the mixture at 0° C. The mixture was stirred at room temperature for 1 hr and then water was added. The separated oil was extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (chloroform-n-hexane, 1/1) to yield 2-(4-chlorophenyl)imino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-one (0.21 g) having a melting point of 53-54° C.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 1 hr
  2. extractionThe separated oil was extracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (chloroform-n-hexane, 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-cd27c9acc26c47ba8554b42114b3e20a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713629B2

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