Imidazole → HCID 20286585, Verbindung

HRID 126879

Reaktionsgleichung

Reaktionsgleichung von HRID 126879
Br[CH:2]([O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][Cl:6].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.[C:23]1([S:37]([OH:40])(=[O:39])=[O:38])[C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([S:33]([OH:36])(=[O:35])=[O:34])[C:27]=2[CH:26]=[CH:25][CH:24]=1>C(#N)C.CC(C)=O>[C:23]1([S:37]([OH:40])(=[O:39])=[O:38])[C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([S:33]([OH:36])(=[O:35])=[O:34])[C:27]=2[CH:26]=[CH:25][CH:24]=1.[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH:2]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][Cl:6])=[CH:12][CH:13]=1

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 66661,5-Naphthalenedisulfonic acidHCID 20286562HCID 20286562, Verbindung

Produkt 1

HCID 20286585HCID 20286585, VerbindungAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

17 g (0.05 mol) of crude 1-bromo-1-(4-chlorophenoxy)-3,3-dimethyl-4-chloro-butan-2-one were dissolved in 100 ml of absolute acetonitrile. 12 g (0.175 mol) of imidazole were added to this solution and the mixture was heated under reflux for 40 hours. Thereafter, it was concentrated by distilling off the solvent in vacuo and the residue was taken up in 300 ml of methylene chloride. The methylene chloride mixture was washed three times with 100 ml of water each time, dried over sodium sulphate and concentrated again in vacuo. The residue was taken up in 100 ml of acetone, and a solution of 9 g (0.038 mol) of 1,5-naphthalenedisulphonic acid in 50 ml of acetone was added. After 2 hours, the precipitate which had formed was filtered off and dried. 19.8 g (80.7% of theory) of 1-(4-chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethyl-4-chloro-butan-2-one naphthalene-1,5-disulphonate of melting point 266°- 267° C. were obtained. ##STR14##

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 40 hours
  3. concentrationThereafter, it was concentrated
  4. distillationby distilling off the solvent in vacuo
  5. washThe methylene chloride mixture was washed three times with 100 ml of water each time
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated again in vacuo
  8. customthe precipitate which had formed
  9. filtrationwas filtered off
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e16aee086878472a9e58aad7c5ba34c4
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254132

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