1,4-Dioxane → HCID 15766694, compound

HRID 1196783Notes

Reaction equation

HRID 1196783 reaction equation
O1CCOCC1.[F:7][C:8]([F:24])([F:23])[C:9]1[C:10]([S:15]([NH:18][C:19](=[O:22])OC)(=[O:17])=[O:16])=[N:11][CH:12]=[CH:13][CH:14]=1.[CH3:25][C:26]1[CH2:30][CH:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[NH:28][N:27]=1>N1C=CC=CC=1>[F:23][C:8]([F:7])([F:24])[C:9]1[C:10]([S:15]([NH:18][C:19]([N:28]2[CH:29]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:30][C:26]([CH3:25])=[N:27]2)=[O:22])(=[O:16])=[O:17])=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 101301011H-Pyrazole, 4,5-dihydro-3-methyl-5-phenyl-HCID 15766693HCID 15766693, compound

Product 1

HCID 15766694HCID 15766694, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A dry dioxane (10 ml) solution containing methyl N-(3-trifluoromethylpyridine-2-sulfonyl)carbamate (0.43 g, 1.5 mmol), 3-methyl-5-phenyl-2-pyrazoline (0.48 g, 3.0 mmol) and pyridine (0.45 g) gas refluxed under heating and stirring for one hour. After cooling the mixture, the solvent was distilled off under reduced pressure, and the residue was stirred together with ethyl ether. Precipitated crystals were collected by filtration and then thoroughly washed with ethyl ether, and the crystals were suspended in 20 ml of water. Then, the pH was adjusted to a level of from 1 to 2 with concentrated hydrochloric acid, and the suspension was stirred at room temperature for 5 minutes. Crystals were collected by filtration, thoroughly washed with water and then with ethyl ether and dried to obtain 0.51 g of desired 1-(3-trifluoromethylpyridine-2-sulfonylcarbamoyl)-3-methyl-5-phenyl-2-pyrazoline. Melting point: 185°-187° C.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating
  3. temperatureAfter cooling the mixture
  4. distillationthe solvent was distilled off under reduced pressure
  5. stirringthe residue was stirred together with ethyl ether
  6. customPrecipitated crystals
  7. filtrationwere collected by filtration
  8. washthoroughly washed with ethyl ether
  9. stirringthe suspension was stirred at room temperature for 5 minutes
  10. filtrationCrystals were collected by filtration
  11. washthoroughly washed with water
  12. dry with materialwith ethyl ether and dried

Sources & evidence

ORD record
ord-d9fd55275816466596875bb22bbf24fa
Source dataset
uspto-grants-1992_05
Patent number
US05116405

Reaction notes

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