Oxalyl chloride → N-methyl-4-pentylbicyclo[2.2.2]octane-1-carboximidoyl chloride
Reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH3:7][NH:8][C:9]([C:11]12[CH2:18][CH2:17][C:14]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH2:15][CH2:16]1)[CH2:13][CH2:12]2)=O>C(Cl)Cl>[CH3:7][N:8]=[C:9]([Cl:4])[C:11]12[CH2:18][CH2:17][C:14]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH2:15][CH2:16]1)[CH2:13][CH2:12]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Oxalyl chloride (846 μL, 9.7 mmol) was added dropwise to a solution of N-methyl-4-pentylbicyclo[2.2.2]octane-1-carboxamide (3-C) (230 mg, 0.97 mmol) in methylene chloride (2.0 mL) and the mixture stirred at room temperature for 4 h. The solvent and excess reagent were removed in vacuo to provide N-methyl-4-pentylbicyclo[2.2.2]octane-1-carboximidoyl chloride (3-D). Toluene (1.5 mL) was added followed by 5-(2-chloro-4-methoxyphenyl)-1H-tetrazole (3-E) (204 mg, 0.97 mmol) and the mixture refluxed for 18 h. The reaction was cooled to room temperature and the precipitate was filtered, washed with cold toluene, hexane, dissolved in methylene chloride, dried (MgSO4) and concentrated in vacuo to provide 3-(2-chloro-4-methoxyphenyl)-4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazole (3-F). Mass spectrum: 402 (M+1); 1H NMR (500 MHz, CDCl3): δ 0.94 (t, 3H); 1.27 (m, 8H); 1.56 (m, 6H); 2.13 (m, 6H); 3.56 (s, 3H); 3.89 (s, 3H); 6.95 (dd, 1H); 7.07 (d, 1H); 7.43 (d, 1H).