Lithium hydroxide, monohydrate → 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylic acid

HRID 75486Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75486
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[N:10]=[C:9]2[CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]=[C:9]2[CH2:18][CH2:19][CH3:20])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 54579226ethyl 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylate2×

Produkt 1

HCID 545792281-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylic acidAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of ethyl 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylate (compound 5, 1.28 g, 4.37 mmol) in THF/water (20/20 mL) was added lithium hydroxide monohydrate at room temperature. The reaction mixture was stirred at 55° C. for 12 hrs. The mixture was washed with CH2Cl2, the aqueous layer was acidified with 1N-HCl solution (pH≈6), extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The obtained product was washed with hexane to provide the title compound (740 mg, 64%) as a pale brown solid.

Aufarbeitung

  1. washThe mixture was washed with CH2Cl2
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe obtained product was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-ded33343f8484d0885807ce27b121196
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835436B2

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