Thioxanthene → 2,7-Bis(3-chloropropionyl)thioxanthene

HRID 436267

Reaktionsgleichung

Reaktionsgleichung von HRID 436267
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:15][CH2:16][CH2:17][C:18](Cl)=[O:19].[Cl-:21].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:15][CH2:16][CH2:17][C:18]([C:10]1[CH:9]=[CH:8][C:7]2[S:6][C:5]3[C:14](=[CH:1][C:2]([C:18](=[O:19])[CH2:17][CH2:16][Cl:21])=[CH:3][CH:4]=3)[CH2:13][C:12]=2[CH:11]=1)=[O:19]

Komponenten

5

Edukt 3

HCID 67495ThioxantheneHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride2×

Produkt 1

HCID 123402872,7-Bis(3-chloropropionyl)thioxanthene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a mixture of 99.2 g (0.5 mole) of thioxanthene, 158.5 g (1.25 mole) of 3-chloropropionyl chloride, and 3 liters of previously dried methylene chloride, chilled to -20° C., is slowly added 146.7 g (1.1 mole) of aluminum chloride over a 30 minute period while maintaining the temperature at below -10° C. Following the addition of aluminum chloride the reaction mixture is slowly permitted to rise to room temperature and then refluxed for an additional 4 hours. The reaction mixture is cooled to room temperature and decomposed by cautiously pouring into 2 liters of an ice-water mixture. The liquid layers are separated and the aqueous layer re-extracted with methylene chloride. The combined organic layers are evaporated to a small volume and cooled. The desired 2,7-bis(3-chloropropionyl)thioxanthene which separates on standing is recrystallized from acetone to yield the desired product having a m.p. of 175°-7° C.

Aufarbeitung

  1. customover a 30 minute
  2. temperaturewhile maintaining the temperature at below -10° C
  3. customto rise to room temperature
  4. temperaturerefluxed for an additional 4 hours
  5. temperatureThe reaction mixture is cooled to room temperature
  6. customThe liquid layers are separated
  7. extractionthe aqueous layer re-extracted with methylene chloride
  8. customThe combined organic layers are evaporated to a small volume
  9. temperaturecooled
  10. customis recrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-9b90296f8fb247eea607471f3415a105
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04008240

Verknüpfte Notizen

Wird geladen…