Oxalyl chloride → N-methyl-4-pentylbicyclo[2.2.2]octane-1-carboximidoyl chloride

HRID 1784488Notes

Reaction equation

HRID 1784488 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]2

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 22591702HCID 22591702, compound

Product 1

HCID 20755112N-methyl-4-pentylbicyclo[2.2.2]octane-1-carboximidoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. customThe solvent and excess reagent were removed in vacuo

Sources & evidence

ORD record
ord-fbb6f3573a304c5fbaff1f0b87a49bad
Source dataset
uspto-grants-2009_03
Patent number
US07504402B2

Reaction notes

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