Chloroacetanilide → HCID 178457010, Verbindung

HRID 38708

Reaktionsgleichung

Reaktionsgleichung von HRID 38708
[H-].[Na+].[CH2:3]([N:6]=[C:7]=[S:8])[CH2:4][CH3:5].Cl[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12].C(OCC)C.CCCCCC>CN(C=O)C>[C:14]1([N:13]2[C:11](=[O:12])[CH2:10][S:8]/[C:7]/2=[N:6]\[CH2:3][CH2:4][CH3:5])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 11485ChloroacetanilideHCID 24758Sodium hydrideHCID 69403Propyl IsothiocyanateHCID 21584099Diethylether hexane

Produkt 1

HCID 178457010HCID 178457010, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

At rt, NaH (154 mg of 55% dispersion in mineral oil, 3.54 mmol) is added in portions to a solution of n-propylisothiocyanate (596 mg, 5.90 mmol) and the above 2-chloro-N-phenyl-acetamide (1000 mg, 5.90 mmol) in DMF (30 mL). Stirring is continued for 2 h after completion of the addition. The mixture is poured onto EA (150 mL) and is extracted twice with 1 N aq. HCl (200 mL). The aq. layer is neutralised by adding 3 N NaOH followed by sat. aq. NaHCO3, and extracted twice with EA (200 mL). The organic extracts are washed with water (200 mL) and evaporated to give a pale yellow, crystalline solid. This material is suspended in a small amount of diethyl ether/hexane 1:1, filtered, washed with additional diethyl ether/hexane and dried under high vacuum to give 3-phenyl-2-[(Z)-propylimino]-thiazolidin-4-one.

Aufarbeitung

  1. additionafter completion of the addition
  2. additionThe mixture is poured onto EA (150 mL)
  3. extractionis extracted twice with 1 N aq. HCl (200 mL)
  4. additionby adding 3 N NaOH
  5. extractionextracted twice with EA (200 mL)
  6. washThe organic extracts are washed with water (200 mL)
  7. customevaporated
  8. customto give a pale yellow, crystalline solid
  9. filtrationfiltered
  10. washwashed with additional diethyl ether/hexane
  11. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5de96110d2c3432d9c3ed8270c8244a2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524752B2

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