Triethylamine → 2-(4-Methoxy-2-methylphenyl)-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-1,3,4-oxadiazole

HRID 22831

Reaction equation

HRID 22831 reaction equation
[Cl-].ClC1N(C)CC[N+]=1C.[CH3:10][C:11]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O.[CH2:22]([C:27]12[CH2:34][CH2:33][C:30]([C:35]([NH:37][NH2:38])=O)([CH2:31][CH2:32]1)[CH2:29][CH2:28]2)[CH2:23][CH2:24][CH2:25][CH3:26].C(N(CC)CC)C>C(Cl)Cl>[CH3:21][O:20][C:18]1[CH:17]=[CH:16][C:12]([C:13]2[O:15][C:35]([C:30]34[CH2:31][CH2:32][C:27]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([CH2:34][CH2:33]3)[CH2:28][CH2:29]4)=[N:37][N:38]=2)=[C:11]([CH3:10])[CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5972164-Methoxy-2-methylbenzoic acidHCID 101763062-Chloro-1,3-dimethylimidazolinium chlorideHCID 225916944-Pentylbicyclo[2.2.2]octane-1-carbohydrazide

Product 1

HCID 225916742-(4-Methoxy-2-methylphenyl)-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-1,3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Chloro-1,3-dimethyl-4,5-dihydro-1H-imidazol-3-ium chloride (5.07 g, 30.0 mmol) was added to a solution of 2-methyl-4-methoxybenzoic acid (2-D) (856 mg, 5.0 mmol) and 4-pentylbicyclo[2.2.2]octane-1-carbohydrazide (2-C) (1.25 g, 5.25 mmol) in methylene chloride (60 mL) followed by triethylamine (8.36 mL, 60 mmol) and the mixture stirred at room temperature for 48 h. The mixture was diluted with methylene chloride and washed with water, 1N HCl, 10% NaHCO3, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hexane:ethyl acetate, 9:1) to give 2-(4-methoxy-2-methylphenyl)-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-1,3,4-oxadiazole (2-E) Mass spectrum: 369 (M+1); 1H NMR (500 MHz, CDCl3): δ 0.93 (t, 3H); 1.27 (m, 8H); 1.56 (m, 6H); 2.03 (m, 6H); 2.70 (s, 3H); 3.89 (s, 3H); 6.86 (m, 2H); 7.89 (d, 1H) ppm.

Workup

  1. washwashed with water, 1N HCl, 10% NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (silica gel, hexane:ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-ec0d9c2fef16467d9d2e421d26e61f1f
Source dataset
uspto-grants-2005_02
Patent number
US06849636B2

Linked notes

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