4'-Methoxyacetophenone → 4-(4-Methoxyphenyl)-1,2,3-thiadiazole

HRID 2372357Notes

Reaction equation

HRID 2372357 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH3:10])=[CH:5][CH:4]=1.C(OC(=O)[NH:16][NH2:17])C.O=[S:20](Cl)Cl>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]=[N:16][S:20][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 74764'-MethoxyacetophenoneHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 24386Thionyl Chloride

Product 1

HCID 27393494-(4-Methoxyphenyl)-1,2,3-thiadiazole

Procedure

The hydrazone (16.0 g, 68 mmol) derived from p-methoxyacetophenone and ethylcarbazate was added to 50 ml of SOCl2 and cooled in an ice bath. The reaction was warmed to room temperature and then heated at 60° C. for 1 hour. The reaction was cooled, and the solvent was removed under vacuum, affording a crude solid. The solid was recrystallized from ether affording 4 (9.95 g, 76%), m.p. 91°-93.5° C.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureheated at 60° C. for 1 hour
  3. temperatureThe reaction was cooled
  4. customthe solvent was removed under vacuum
  5. customaffording a crude solid
  6. customThe solid was recrystallized from ether affording 4 (9.95 g, 76%), m.p. 91°-93.5° C.

Sources & evidence

ORD record
ord-d1bc08589faa4efab65cb95e3d3881f5
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

Loading…