2,6-Difluoroaniline → Flumetsulam

HRID 1031364Notes

Reaction equation

HRID 1031364 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[CH3:10][C:11]1[CH:16]=[CH:15][N:14]2[N:17]=[C:18]([S:20](Cl)(=[O:22])=[O:21])[N:19]=[C:13]2[N:12]=1>N1C=CC=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][N:14]2[N:17]=[C:18]([S:20]([NH:4][C:3]3[C:2]([F:1])=[CH:8][CH:7]=[CH:6][C:5]=3[F:9])(=[O:22])=[O:21])[N:19]=[C:13]2[N:12]=1

Participants

4

Reactant 2

HCID 796472,6-DifluoroanilineHCID 141551085-Methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chloride

Product 1

HCID 91759FlumetsulamYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The starting 2,6-difluoroaniline (18.1 g, 0.140 mol) was dissolved in 45 ml of pyridine and 36.1 g (0.155 mol) of 5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride was added. After an exothermic reaction subsided the reaction mixture was stirred at room temperature for 15.5 hours. The pyridine was removed by evaporation at reduced pressure, and the residue was treated with 600 ml of 0.5N NaOH. After stirring to dissolve all soluble material the mixture was filtered through celite and the filtrate was acidified with 3N HCl. The precipitate which separated upon acidification was collected by filtration and dried to yield 33.0 g (73%) of the desired product as a pale red solid, m.p. 245°-247° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. customAfter an exothermic reaction
  2. customThe pyridine was removed by evaporation at reduced pressure
  3. additionthe residue was treated with 600 ml of 0.5N NaOH
  4. stirringAfter stirring
  5. dissolutionto dissolve all soluble material the mixture
  6. filtrationwas filtered through celite
  7. customThe precipitate which separated upon acidification
  8. filtrationwas collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-20acd67d9cf54d6bb805b85c1b6cffb8
Source dataset
uspto-grants-1990_09
Patent number
US04954163

Reaction notes

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