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

HRID 276138

Reaktionsgleichung

Reaktionsgleichung von HRID 276138
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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 sulphate 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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-8bd6ca3e25f7461e8885dbd7a7f0f54c
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353117B1

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