O-Xylene → 4,8-Bis(trifluoromethyl)-10,11-dihydrodibenzo[b,f][1,4]thiazepin-11-one

HRID 1082075

Reaktionsgleichung

Reaktionsgleichung von HRID 1082075
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12][C:13]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#N.[OH-:25].[Na+].C1(C)C(C)=CC=CC=1>C(O)(=O)C.S(=O)(=O)(O)O.O>[F:23][C:21]([F:24])([F:22])[C:20]1[C:13]2[S:12][C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=3[NH:1][C:15](=[O:25])[C:14]=2[CH:17]=[CH:18][CH:19]=1

Komponenten

7

Edukt 3

HCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 199694362-(2-Amino-4-trifluoromethylphenylthio)-3-trifluoromethylbenzonitrile

Produkt 1

HCID 199694574,8-Bis(trifluoromethyl)-10,11-dihydrodibenzo[b,f][1,4]thiazepin-11-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

2-(2-Amino-4-trifluoromethylphenylthio)-3-trifluoromethylbenzonitrile (5.43 g, 15 mmol) was dissolved in a mixture of glacial acetic acid (60 ml), concentrated sulphuric acid (55 ml) and water (60 ml) and then heated under reflex for 8 hours. The cooled mixture was added to ice water (500 ml) and brought to pH 4 by addition of 10N aqueous sodium hydroxide. Extraction with dichloromethane followed by filtration, drying (sodium sulphate) and evaporation of the organic layer afforded a residue which was put into xylene (500 ml) and refluxed for 72 hours with azeotropic removal of water. The resulting solution was evaporated and the residue was recrystallised twice from ethanol to give the product as colourless needles (4.30 g, m/s, M+ =363).

Aufarbeitung

  1. temperatureheated under reflex for 8 hours
  2. extractionExtraction with dichloromethane
  3. filtrationfollowed by filtration
  4. customdrying
  5. custom(sodium sulphate) and evaporation of the organic layer
  6. customafforded a residue which
  7. customThe resulting solution was evaporated
  8. customthe residue was recrystallised twice from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-63e5b92100d649e4abe24fe83234f05b
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05589474

Verknüpfte Notizen

Wird geladen…