Hydrochloric Acid → HCID 23118574, compound

HRID 2375443Notes

Reaction equation

HRID 2375443 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:13](C(OCC)=O)[S:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.Cl>O>[S:12]1[CH:13]=[N:14][C:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)=[N:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23118573HCID 23118573, compound

Product 1

HCID 23118574HCID 23118574, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl cianoformate was added to a dodecane suspension of 5-(4-nitrophenyl)-1,3,4-oxathiazol-2-on, and the mixture was refluxed under heating for 3 hours. After cooling the reaction mixture to room temperature, the precipitation was separated by filtration and washed with hexane. The crude product obtained was purified by silica gel column chromatography to obtain ethyl 3-(4-nitrophenyl)-1,2,4-thiadiazole-5-carboxylate (pale yellow solid). The ethanol suspension of this product was added with water and sodium hydroxide and heated at 85° C. for 40 minutes while stirring. After cooling to room temperature, the mixture was added with 1M hydrochloric acid to make it acidic. The resulting mixture was heated for one hour while stirring on an oil bath at 95° C. The mixture was then cooled to room temperature and added with chloroform and an aqueous sodium hydrogencarbonate to separate an organic layer, which was then washed and dried. The solvent was evaporated under reduced pressure to obtain 3-(4-nitrophenyl)-1,2,4-thiadiazol (pale yellow solid). The ethanol suspension of this product was added with water and 1M hydrochloric acid, heated to 80° C. and added with reduced iron. The reaction mixture was further heated at 80° C. for 50 minutes while stirring and then filtered through Celite. After evaporation of the ethanol in the resulting filtrate under reduced pressure, chloroform and an aqueous sodium hydrogencarbonate were added to the residue to separate an organic layer, which was then washed and dried. The solvent was evaporated under reduced pressure to obtain 4-(1,2,4-thiadiazol-3-yl)aniline (pale yellow solid). Electron Impact-MS (M)+: 177.

Workup

  1. temperatureThe reaction mixture was further heated at 80° C. for 50 minutes
  2. filtrationfiltered through Celite
  3. customAfter evaporation of the ethanol in the resulting filtrate under reduced pressure, chloroform
  4. additionan aqueous sodium hydrogencarbonate were added to the residue
  5. customto separate an organic layer, which
  6. washwas then washed
  7. customdried
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-db7cf85ba7b54be7961cd44c97da9825
Source dataset
uspto-grants-2008_12
Patent number
US07465748B2

Reaction notes

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