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

HRID 275039Notes

Reaction equation

HRID 275039 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 167 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-31c4de89595b42dca2ca02089284f578
Source dataset
uspto-grants-1995_02
Patent number
US05391759

Reaction notes

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