반응 #466214

반응 방정식

4-chlorophenethyl alcohol

triethylamine

methanesulfonyl chloride

2-hydroxy-4-imidazol-1-ylmethyl-benzonitrile

cesium carbonate

→

title compound

2-(4-Chlorophenyl-2-ethoxy)-4-imidazol-1-ylmethyl-benzonitrile Hydrochloride

CH3OH NH4OH

수율 0.1%

용매

CH2Cl2

DMF

반응 조건

후처리

1. 1
   농축The reaction mixture was concentrated in vacuo
2. 2
   workup.DISSOLUTIONdissolved in DMF (1 mL)
3. 3
   온도The reaction mixture was heated at 30° C. for 18 h
4. 4
   기타partitioned between EtOAc and H2O
5. 5
   세척the aqueous layer washed with EtOAc
6. 6
   세척washed with brine
7. 7
   건조dried (Na2SO4)
8. 8
   여과Filtration and concentration to dryness

실험 절차

4-chlorophenethyl alcohol (0.11 g, 0.67 mmol) and triethylamine (0.37 mL, 2.68 mmol) were dissolved in CH2Cl2 (5 mL) at 0° C. Then it was treated with methanesulfonyl chloride (0.207 mL, 2.68 mmol), with stirring and warming to ambient temperature, until the indicated loss of starting material. The reaction mixture was concentrated in vacuo, then dissolved in DMF (1 mL) and added to a mixture of 2-hydroxy-4-imidazol-1-ylmethyl-benzonitrile (0.10 g, 0.50 mmol) and cesium carbonate (0.33 g, 1.0 mmol) in DMF (2 mL). The reaction mixture was heated at 30° C. for 18 h, then partitioned between EtOAc and H2O, the aqueous layer washed with EtOAc, the organic layers combined, washed with brine, and dried (Na2SO4). Filtration and concentration to dryness gave the title compound after silica gel chromatography (0.1 to 0.2% CH3OH/NH4OH in CH2Cl2) and conversion to the hydrochloride salt.

출처