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

HRID 2372356

Reaction equation

HRID 2372356 reaction equation
[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

Participants

3

Reactant 2

HCID 99482-PhenylacetophenoneHCID 675181,2,3-Thiadiazole

Product 1

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

Procedure

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).

Workup

  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.

Sources & evidence

ORD record
ord-2b10a8cca8ed49258f3610bc8b4593a1
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Linked notes

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