Hydrochloric Acid → N-(2,6-Difluorophenyl)-5-formylamino-1,2,4-triazole-3-sulfonamide

HRID 1655041Notes

Reaction equation

HRID 1655041 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[CH:10]([NH:12][C:13]1[NH:17][N:16]=[C:15]([S:18](Cl)(=[O:20])=[O:19])[N:14]=1)=[O:11].[OH-].[Na+].Cl>N1C=CC=CC=1.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH:4][S:18]([C:15]1[N:14]=[C:13]([NH:12][CH:10]=[O:11])[NH:17][N:16]=1)(=[O:19])=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 796472,6-DifluoroanilineHCID 178522608HCID 178522608, compound

Product 1

HCID 178522611N-(2,6-Difluorophenyl)-5-formylamino-1,2,4-triazole-3-sulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 1.3 g (10 mmol) of 2,6-difluoroaniline in 4 ml of pyridine was added 1.94 g (9.2 mmol) of 5-formylamino-3-chlorosulfonyl-1,2,4-triazole over a period of 5 minutes. The mixture was heated with stirring to 70° C. for 4 hours. It was then cooled and dispersed between 25 ml of 1N aqueous sodium hydroxide and 50 ml of chloroform. The aqueous layer was acidified with aqueous hydrochloric acid and filtered. The solids collected were dried to obtain 1.67 g (60 percent of theory) of the title compound, m.p. 258°-260° C. The infrared spectrum was consistent, with the assigned structure.

Workup

  1. temperatureThe mixture was heated
  2. temperatureIt was then cooled
  3. filtrationfiltered
  4. customThe solids collected
  5. customwere dried

Sources & evidence

ORD record
ord-89e4ba369f8146f2b2ed3a037f02d47f
Source dataset
uspto-grants-1995_04
Patent number
US05410065

Reaction notes

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