2,6-Difluoroaniline → HCID 14155228, compound

HRID 844979Notes

Reaction equation

HRID 844979 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[Cl:10][C:11]1[CH:12]=[N:13][C:14]2[N:15]([N:17]=[C:18]([S:20](Cl)(=[O:22])=[O:21])[N:19]=2)[CH:16]=1>N1C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[N:13][C:14]2[N:15]([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]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 796472,6-DifluoroanilineHCID 14155106HCID 14155106, compound

Product 1

HCID 14155228HCID 14155228, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The starting 2,6-difluoroaniline (1.7 g, 13 mmol) was dissolved in 3.5 ml of pyridine and 3.5 g (14 mmol) of 6-chloro-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride was added. After an exothermic reaction subsided the reaction mixture was heated at 60°-70° C. overnight. The solvent was removed by evaporation at reduced pressure and the residue was taken up in aqueous sodium bicarbonate. The aqueous solution was washed with ether, and acidified with acqueous HCl. The solid which separated upon acidification was collected by filtration, dried and recrystallized from methanol to afford 2.5 g (55%) of the desired product as a crystalline solid, m.p. 224°-226° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. customAfter an exothermic reaction
  2. temperaturewas heated at 60°-70° C. overnight
  3. customThe solvent was removed by evaporation at reduced pressure
  4. washThe aqueous solution was washed with ether
  5. customThe solid which separated upon acidification
  6. filtrationwas collected by filtration
  7. customdried
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-bef137474e2149ce93fdcd3cdfa3859d
Source dataset
uspto-grants-1988_07
Patent number
US04755212

Reaction notes

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