Pyridine → N-(2,6-Dichloro-3-methylphenyl)-5-formylamino-1,2,4-triazole-5-sulfonamide

HRID 1655042

Reaction equation

HRID 1655042 reaction equation
[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([Cl:10])[C:3]=1[NH2:4].C(N[C:14]1[NH:18][N:17]=[C:16]([S:19](Cl)(=[O:21])=[O:20])[N:15]=1)=O.[OH-:23].[Na+].C(Cl)(Cl)Cl.[N:29]1[CH:34]=CC=CC=1>>[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([Cl:10])[C:3]=1[NH:4][S:19]([C:16]1([NH:29][CH:34]=[O:23])[N:17]=[N:18][CH:14]=[N:15]1)(=[O:20])=[O:21]

Participants

6

Reactant 5

HCID 1049PyridineHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 1165292,6-Dichloro-3-methylanilineHCID 178522608HCID 178522608, compound

Product 1

HCID 20077588N-(2,6-Dichloro-3-methylphenyl)-5-formylamino-1,2,4-triazole-5-sulfonamide

Conditions

Temperature
70 °C

Procedure

To a mixture of 1 g (5.2 mmol) of 2,6-dichloro-3-methylaniline in 2 ml pyridine was added 1 g (4.7 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 recovered, extracted with more chloroform, and acidified with aqueous hydrochloric acid. The solids that formed were collected by filtration and dried to obtain 1.0 g (59 percent of theory) of the title compound, m.p. 275°-279° C. The infrared and carbon nmr spectra were consistent with the assigned structure.

Workup

  1. temperatureThe mixture was heated
  2. temperatureIt was then cooled
  3. customThe aqueous layer was recovered
  4. extractionextracted with more chloroform
  5. customThe solids that formed
  6. filtrationwere collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-ea6e1cc13e1a424fa7edfc10e98d12af
Source dataset
uspto-grants-1995_04
Patent number
US05410065

Linked notes

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