Imidazole → 1-(1,2,3,4-Tetrahydronaphthalen-2-yl)imidazole
Reaction equation
CS(O[CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)(=O)=O.[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1>CN(C=O)C>[CH2:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH2:15][CH:6]1[N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
A mixture of 1,2,3,4-tetrahydronaphthalen-2-yl methanesulfonate (15.74 g, 69.6 mmol), prepared as in Example 7, and imidazole (23.68 g, 349 mmol) in 100 mL of DMF was heated at 80 to 90° C. under argon for 24 hours. The solvent was removed under vacuum by rotary evaporation. The residue was dissolved in 500 mL of ethyl acetate and the solution was washed with water (5×250 mL). The combined aqueous layer was extracted with 500 mL of ethyl acetate and the extract was then washed with water (5×250 mL). The combined ethyl acetate extract was washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated by rotary evaporation. Purification of the residue by column chromatography on silica gel (elution: 5% methanol/methylene chloride) gave 1-(1,2,3,4-tetrahydronaphthalen-2-yl)imidazole (5.18 g, 26.1 mmol), m.p. 93°-95° C.