4-Bromo-3-methylaniline → N-(3-(((4-bromo-3-methylphenyl)amino)sulfonyl)-1H-1,2,4-triazol-5-yl)formamide

HRID 2108177Notes

Reaction equation

HRID 2108177 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[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].S(Cl)(Cl)(=O)=O>C(#N)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:18]([C:15]2[N:14]=[C:13]([NH:12][CH:10]=[O:11])[NH:17][N:16]=2)(=[O:19])=[O:20])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 233594-Bromo-3-methylanilineHCID 24648Sulfuryl chlorideHCID 178522608HCID 178522608, compound

Product 1

HCID 178428786N-(3-(((4-bromo-3-methylphenyl)amino)sulfonyl)-1H-1,2,4-triazol-5-yl)formamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-bromo-3-methylaniline (3.72 g, 20 mmol) and 5-formamido-1,2,4-triazole-3-sulfonyl chloride (2.10 g, 10 mmol) in 50 mL of acetonitrile was refluxed under nitrogen until all of the sulfonyl chloride has been consumed (approximately 1 hr). The mixture was cooled and filtered. The precipitate was dispersed in 200 mL of 1% aqueous HCl solution and filtered again to yield the title compound as a white solid, 3.0 g (84%) m.p. 282°-284° C., M+ -Br at 280.

Workup

  1. customhas been consumed (approximately 1 hr)
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. additionThe precipitate was dispersed in 200 mL of 1% aqueous HCl solution
  5. filtrationfiltered again

Sources & evidence

ORD record
ord-8095382c526441548252a8d91799e373
Source dataset
uspto-grants-1990_06
Patent number
US04937350

Reaction notes

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