Hydrochloric Acid → HCID 178423885, Verbindung

HRID 325954

Reaktionsgleichung

Reaktionsgleichung von HRID 325954
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].C[O-].[Na+].Cl[CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1.Cl>CO.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9])[CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 113352,6-DimethylphenolHCID 10942334Sodium MethoxideHCID 178478442HCID 178478442, Verbindung

Produkt 1

HCID 178423885HCID 178423885, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 12.2 g of 2,6-dimethylphenol in methanol are added 20 ml of 30% sodium methoxide solution, and the resultant mixture is warmed to 50° C. The mixture is maintained at that temperature while 5.8 g of 4-chloromethylimidazole in methanol are added, with stirring. After the addition is complete, the reaction mixture is stirred at 50°-60° C. for about 4 hours, then is cooled and poured into cold water. That mixture is acidified with hydrochloric acid and washed with ethyl acetate. The pH of the aqueous solution is then adjusted to 7-8, and the product is obtained by extraction with ethyl acetate. The desired 4-(3',5'-dimethyl-4'-hydroxybenzyl)imidazole is obtained in 54% yield. The free base is converted to the corresponding hydrochloride salt by treatment with HCl in a mixture of ethyl acetate and isopropanol. That salt melts at 210°-214° C.

Aufarbeitung

  1. additionare added
  2. additionAfter the addition
  3. stirringthe reaction mixture is stirred at 50°-60° C. for about 4 hours
  4. temperatureis cooled
  5. washwashed with ethyl acetate
  6. customthe product is obtained by extraction with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f69cbcaa3b7a486384a48415704c70e6
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04443466

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