2-Phenylacetophenone → 4,5-Diphenyl-1,2,3-thiadiazole

HRID 2372356

Reaktionsgleichung

Reaktionsgleichung von HRID 2372356
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:16]1C=C[N:18]=[N:17]1>>[C:1]1([C:7]2[N:18]=[N:17][S:16][C:8]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

3

Edukt 2

HCID 99482-PhenylacetophenoneHCID 675181,2,3-Thiadiazole

Produkt 1

HCID 2201694,5-Diphenyl-1,2,3-thiadiazole

Versuchsvorschrift

The tosylhydrazone (58.0 g, 0.16 mol) was dissolved in CH2Cl2 (200 ml) and thionyl chloride (14.1 ml, 0.2 mol) in CH2Cl2 (10 ml) was added and the entire reaction was stirred at room temperature 2.25 hours. Filtration of the mixture afforded 9.0 g of solid identified by NMR as toluenesulfonylchloride. The remaining liquid was concentrated and then heated at reflux in THF (200 ml) and H2O (50 ml) for 20.5 hours. After cooling, it was brought to pH 11 with NaOH. The aqueous layer was extracted with 2×50 ml portions of Et2O. Drying and evaporation yielded 34 g of solid material. This was recrystallized from hexane to afford 3 (7.5 g, 46%), m.p. 92°-94° C. A second crop from recrystallization afforded additional amounts of 3 (6.9 g) contaminated with a-phenylacetophenone. The thiadiazole could be sublimed at 110° C. (0.2 mm).

Aufarbeitung

  1. customThis was recrystallized from hexane
  2. customto afford 3 (7.5 g, 46%), m.p. 92°-94° C
  3. customA second crop from recrystallization
  4. customafforded additional amounts of 3 (6.9 g)
  5. customcould be sublimed at 110° C.

Quellen und Nachweise

ORD-Eintrag
ord-2b10a8cca8ed49258f3610bc8b4593a1
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05098918

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