Sulfur → Fluproquazone

HRID 1075302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1075302
[CH:1]([N:4]1[CH:13]2[CH:8]([CH2:9][CH2:10][C:11]([CH3:14])=[CH:12]2)[C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:6][C:5]1=[O:22])([CH3:3])[CH3:2].[S]>C1C2C(CCCC2)CCC1.C1(C)C=CC=CC=1>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[CH:12]=2)[C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:6][C:5]1=[O:22])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 5362487SulfurHCID 20494720HCID 20494720, Verbindung

Produkt 1

HCID 38503Fluproquazone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 7044DecalinLösungsmittel

Versuchsvorschrift

17.4 g 1-isopropyl-4-(4-fluorophenyl)-7-methyl-4a,5,6,8a-tetrahydro-2(1H)-quinazolinone are dissolved under heating in 50 ml decaline and treated portionwise at 140° with 4 g powdered sulphur. On completion of the addition stirring is continued for 1 hour at 160°. The mixture is diluted with toluene and extracted several times with 15% hydrochloric acid. The acidic phase is treated with methylene chloride and neutralized under ice cooling with sodium hydroxide solution. The water phase is extracted with methylene chloride and the combined methylene chloride extracts concentrated in vacuo. The concentrate is chromatographed on silica gel using dichloromethane and methanol as eluant. After recrystallisation from toluene the title compound is obtained, m.p. 174°-176°.

Aufarbeitung

  1. additiontreated portionwise at 140° with 4 g
  2. additionOn completion of the addition
  3. extractionextracted several times with 15% hydrochloric acid
  4. additionThe acidic phase is treated with methylene chloride and neutralized under ice cooling with sodium hydroxide solution
  5. extractionThe water phase is extracted with methylene chloride
  6. concentrationthe combined methylene chloride extracts concentrated in vacuo
  7. customThe concentrate is chromatographed on silica gel
  8. customAfter recrystallisation from toluene the title compound
  9. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-8ac7b3ca34b04198ba0b69402f46bc29
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04395550

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