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

HRID 276139

反応式

HRID 276139 の反応式
[F:1][C:2]([F:16])([F:15])[C:3](=O)/[CH:4]=[C:5](\[CH3:13])/[C:6]1[CH:11]=[CH:10][C:9](C)=[CH:8][CH:7]=1.[NH2:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][NH2:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19].N1CCCCC1.O>C(O)C>[NH2:17][S:18]([C:21]1[CH:22]=[CH:23][C:24]([N:27]2[C:5]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)([CH3:13])[CH2:4][C:3]([C:2]([F:1])([F:15])[F:16])=[N:28]2)=[CH:25][CH:26]=1)(=[O:20])=[O:19]

参加物

6

反応物 4

HCID 962WaterHCID 8082PiperidineHCID 78105p-HydrazinobenzenesulphonamideHCID 15484795HCID 15484795、化合物

生成物 1

HCID 99519581-(4-aminosulphonylphenyl)-4,5-dihydro-5-phenyl-5-methyl-3-trifluoromethyl-1H-pyrazole

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

In a flask with an inert atmosphere (E)-1,1,1-trifluoro-4-methyl-4-(4-methylphenyl)-3-butene-2-one (1.75 g, 8.2 mmoles), 4-(aminosulphonyl)phenylhydrazine chlorohydrate (2 g, 9 mmoles) and piperidine (0.85 g, 10 mmoles) are added, dissolved in 100 ml of ethanol, and heated under reflux for 5.5 hours. The mixture is cooled, the solvent eliminated with a rotovapor, water added to the residue and the solution extracted with AcOEt. The organic phase is washed with water, dried over anhydrous sodium sulphate and evaporated to dryness. The crude product is purified using column chromatography through silica gel under pressure, eluting with AcOEt-petrol ether (4:6) obtaining 1-(4-aminosulphonylphenyl)-4,5-dihydro-5-phenyl-5-methyl-3-trifluoromethyl-1H-pyrazole in the form of a white solid (1.46 g, yield: 47%) with a

後処理

  1. temperatureheated
  2. temperatureunder reflux for 5.5 hours
  3. temperatureThe mixture is cooled
  4. additionadded to the residue
  5. extractionthe solution extracted with AcOEt
  6. washThe organic phase is washed with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated to dryness
  9. customThe crude product is purified
  10. washeluting with AcOEt-petrol ether (4:6)

出典と根拠

ORDレコード
ord-ae3af41bb47f499487602c6b579445f8
出典データセット
uspto-grants-2002_03
特許番号
US06353117B1

関連ノート

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