Hydrochloric Acid → HCID 23118575, compound

HRID 2375442Notes

Reaction equation

HRID 2375442 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-:3])=[O:2].O.[OH-].[Na+].Cl>C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]=[CH:13][S:12][N:11]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23118573HCID 23118573, compound

Product 1

HCID 23118575HCID 23118575, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
85 °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. temperatureAfter cooling to room temperature
  2. temperatureThe resulting mixture was heated for one hour
  3. stirringwhile stirring on an oil bath at 95° C
  4. temperatureThe mixture was then cooled to room temperature
  5. customan aqueous sodium hydrogencarbonate to separate an organic layer, which
  6. washwas then washed
  7. customdried
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ae534297b2984e6ca55be2b62c305b46
Source dataset
uspto-grants-2008_12
Patent number
US07465748B2

Reaction notes

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