Imidazole → HCID 20286594, Verbindung

HRID 127241

Reaktionsgleichung

Reaktionsgleichung von HRID 127241
Br[CH:2]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][Cl:6].[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.[C:29]1([S:43]([OH:46])(=[O:45])=[O:44])[C:38]2[CH:37]=[CH:36][CH:35]=[C:34]([S:39]([OH:42])(=[O:41])=[O:40])[C:33]=2[CH:32]=[CH:31][CH:30]=1>C(#N)C.CC(C)=O>[C:29]1([S:43]([OH:46])(=[O:45])=[O:44])[C:38]2[CH:37]=[CH:36][CH:35]=[C:34]([S:39]([OH:42])(=[O:41])=[O:40])[C:33]=2[CH:32]=[CH:31][CH:30]=1.[Cl:6][CH2:5][C:4]([CH3:8])([CH3:7])[C:3](=[O:9])[CH:2]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 66661,5-Naphthalenedisulfonic acidHCID 20286578HCID 20286578, Verbindung

Produkt 1

HCID 20286594HCID 20286594, VerbindungAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

20.8 g (0.05 mol) of crude 1-bromo-4-chloro-1-[4-(4-chlorophenyl)-phenoxy]-3,3-dimethyl-butan-2-one were dissolved in 120 ml of absolute acetonitrile. 12 g (0.175 mol) of imidazole were added and the mixture was heated for 40 hours under reflux. It was then concentrated by distilling off the solvent in vacuo and the residue was taken up in 300 ml of methylene chloride. The solution was washed three times with 100 ml of water at a time and was dried over sodium sulphate and again concentrated 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 formed was filtered off and dried. 19.6 g (72% of theory) of 4-chloro-1-[4-(4-chlorophenyl)-phenoxy]-3,3-dimethyl-1(imidazol-1-yl)-butan-2-one naphthalene-1,5-disulphonate of melting point 246° C. were obtained.

Aufarbeitung

  1. temperaturethe mixture was heated for 40 hours
  2. temperatureunder reflux
  3. concentrationIt was then concentrated
  4. distillationby distilling off the solvent in vacuo
  5. washThe solution was washed three times with 100 ml of water at a time
  6. dry with materialwas dried over sodium sulphate
  7. concentrationagain concentrated in vacuo
  8. customthe precipitate formed
  9. filtrationwas filtered off
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2bd6031018d24b218f83506fc1e70011
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04255434

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