Sodium Chloride → 1-Benzyl-alpha,alpha-bis(p-chlorophenyl)imidazole-2-methanol

HRID 261967

Reaktionsgleichung

Reaktionsgleichung von HRID 261967
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([Li])C=CC=CC=1.[Li].BrC1C=CC=CC=1.[Cl:28][C:29]1[CH:43]=[CH:42][C:32]([C:33]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)=[O:34])=[CH:31][CH:30]=1.[Cl-].[Na+]>O1CCCC1.C(OCC)C>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:33]([C:32]1[CH:42]=[CH:43][C:29]([Cl:28])=[CH:30][CH:31]=1)([C:35]1[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=1)[OH:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

9

Edukt 6

HCID 5234Sodium ChlorideHCID 70344,4'-DichlorobenzophenoneHCID 7961BromobenzeneHCID 779181-BenzylimidazoleHCID 3028194LithiumHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 124339381-Benzyl-alpha,alpha-bis(p-chlorophenyl)imidazole-2-methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 17.4 g (0.11 mol) of N-benzylimidazole in 40 ml. of anhydrous tetrahydrofuran was added dropwise in the course of one hour, at -20° to -30° C. and under a nitrogen atmosphere, to a phenyl lithium solution, prepared from 1.67 g (0.24 gr. at.) of lithium and 18.8 g (0.12 mol) of bromobenzene in 80 ml. of anhydrous diethyl ether. The mixture was heated for about one hour until a brightly red, homogenous solution was obtained. Subsequently a solution of 25.1 g (0.1 mol) of 4,4'-dichlorobenzophenone in 60 ml. of anhydrous tetrahydrofuran was added in the course of one hour at a temperature between -25° and -15° C. The reaction mixture was stirred for 15 hours at room temperature, under the nitrogen atmosphere and it was then poured on 200 g of ice. The aqueous phase was saturated with sodium chloride and the organic phase was separated off and concentrated. The residue was dissolved in a small amount of acetone and the solution was acidified with 2 N hydrochloric acid. Then some toluene was added and the precipitate formed was filtered off. The product was thrice crystallised from a mixture of isopropyl alcohol and petroleum ether (boiling range 28°-40° C.). 1-Benzyl-α,α-bis(p-chlorophenyl)imidazole-2-methanol was obtained. Melting point 167°-168° C.

Aufarbeitung

  1. temperatureThe mixture was heated for about one hour until a brightly red, homogenous solution
  2. customwas obtained
  3. customthe organic phase was separated off
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in a small amount of acetone
  6. additionThen some toluene was added
  7. customthe precipitate formed
  8. filtrationwas filtered off
  9. customcrystallised from a mixture of isopropyl alcohol and petroleum ether (boiling range 28°-40° C.)

Quellen und Nachweise

ORD-Eintrag
ord-b80c368add57420dbc5a6e50cd05ee63
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04152441

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