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

HRID 22831

반응식

HRID 22831 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ec0d9c2fef16467d9d2e421d26e61f1f
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849636B2

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