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

HRID 22836Notes

Reaction equation

HRID 22836 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-561648bdfe4845d8989c9c5b75f8b2c7
Source dataset
uspto-grants-2005_02
Patent number
US06849636B2

Reaction notes

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