Benzene → HCID 12912194, Verbindung

HRID 461600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 461600
[CH2:1]([N:4]1[C:8]([OH:9])=[C:7]([C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[C:6]([CH3:20])=[N:5]1)[CH:2]=[CH2:3].C1C=CC=CC=1.C(N(CC)CC)C.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>O>[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([O:9][C:8]2[N:4]([CH2:1][CH:2]=[CH2:3])[N:5]=[C:6]([CH3:20])[C:7]=2[C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])(=[O:42])=[O:41])=[CH:36][CH:35]=1

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178456657HCID 178456657, Verbindung

Produkt 1

HCID 12912194HCID 12912194, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 180 mg. of 1-allyl-3-methyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole in 6 ml. of benzene and 58.4 mg. of triethylamine is added dropwise 110 mg. of 4-toluenesulfonyl chloride with stirring at room temperature. Then, the resulting mixture is heated under reflux for 1 hour. After completion of the reaction, water is added to the reaction mixture and an organic layer is separated. The organic layer is dried over anhydrous sodium sulfate, the solvent is distilled off and the resulting oily substance is recrystallized from benzene-n-hexane to give 173 mg. of the desired product as colorless prisms melting at 113°-114° C. Further, the solvent is distilled off from the mother liquor and recrystallization from n-hexane gives 26 mg. of the desired product. Total yield 73.9%

Aufarbeitung

  1. temperatureThen, the resulting mixture is heated
  2. temperatureunder reflux for 1 hour
  3. additionis added to the reaction mixture
  4. customan organic layer is separated
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. distillationthe solvent is distilled off
  7. customthe resulting oily substance is recrystallized from benzene-n-hexane
  8. customto give 173 mg

Quellen und Nachweise

ORD-Eintrag
ord-4150a449d6e94c079376acee5f00c1f6
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04063925

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