Water → 1-(4-aminosulphonylphenyl)-4,5-dihydro-5-(4-methylphenyl)-3-trifluoromethyl-1H-pyrazole

HRID 1611858Notes

Reaction equation

HRID 1611858 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:13][C:14]([F:27])([F:26])[C:15](=O)/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1.O>C(O)(=O)C>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:17]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)[CH2:16][C:15]([C:14]([F:13])([F:26])[F:27])=[N:12]2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 78105p-HydrazinobenzenesulphonamideHCID 11206657HCID 11206657, compound

Product 1

HCID 99519571-(4-aminosulphonylphenyl)-4,5-dihydro-5-(4-methylphenyl)-3-trifluoromethyl-1H-pyrazoleYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-(aminosulphonyl)phenylhydrazine chlorohydrate (0.82 g, 3.69 mmoles) and (E)-1,1,1-trifluoro-4-(4-methylphenyl)-3-butene-2-one (0.79 g, 3.69 mmoles) in 15 ml of acetic acid is refluxed for 3 hours under a nitrogen atmosphere. It is cooled, poured over water and extracted with AcOEt. The organic solution is washed with water, dried over anhydrous sodium sulphatic and evaporated to dryness under vacuum. The crude product thus obtained is crystallised from EtOH-petrol ether to give 1-(4-aminosulphonylphenyl)-4,5-dihydro-5-(4-methylphenyl)-3-trifluoromethyl-1H-pyrazole (0.65 g, yield: 45%).

Workup

  1. temperatureIt is cooled
  2. extractionextracted with AcOEt
  3. washThe organic solution is washed with water
  4. dry with materialdried over anhydrous sodium sulphatic
  5. customevaporated to dryness under vacuum
  6. customThe crude product thus obtained
  7. customis crystallised from EtOH-petrol ether

Sources & evidence

ORD record
ord-7bfdefa69557408e9c688f28031f52e3
Source dataset
uspto-grants-2006_01
Patent number
USRE038963E1

Reaction notes

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