Pyridine → 1-(2,6-Dichloro-4-trifluoromethylphenyl)-5-(2-tetrahydrofuroyl)-amino-pyrazole

HRID 622594Notes

Reaction equation

HRID 622594 reaction equation
N[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[CH:4][CH:3]=1.[N:19]1C=CC=CC=1.[O:25]1[CH2:29][CH2:28][CH2:27][CH:26]1[C:30](Cl)=[O:31]>C(#N)C>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]([C:30]([CH:26]2[CH2:27][CH2:28][CH2:29][O:25]2)=[O:31])=[CH:3][C:4]([NH2:19])=[N:5]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 551254Tetrahydro-2-furancarbonyl chlorideHCID 135571095-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole

Product 1

HCID 212911501-(2,6-Dichloro-4-trifluoromethylphenyl)-5-(2-tetrahydrofuroyl)-amino-pyrazoleYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

19.8 g (0.07 mol) of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole and 7.1 g (0.09 mol) of pyridine are dissolved in 150 ml of acetonitrile, and 12.1 g (0.09 mol) of tetrahydrofuran-2-carboxylic acid chloride are added at 25°-30° C., with stirring. The mixture is stirred at room temperature for a further 24 hours. The reaction batch is then poured onto water and extracted with chloroform; the chloroform phase is washed with aqueous sodium bicarbonate solution, dried over sodium sulphate and concentrated. The oily residue is crystallized by trituration with petroleum ether. 24 g (87% of theory) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(2-tetrahydrofuroyl)-amino-pyrazole of melting point 95°-97° C. are obtained.

Workup

  1. stirringThe mixture is stirred at room temperature for a further 24 hours
  2. additionThe reaction batch is then poured onto water
  3. extractionextracted with chloroform
  4. washthe chloroform phase is washed with aqueous sodium bicarbonate solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe oily residue is crystallized by trituration with petroleum ether

Sources & evidence

ORD record
ord-c6a25f4a19c54ab4ae73800a02559cf6
Source dataset
uspto-grants-1988_09
Patent number
US04772309

Reaction notes

Loading…