Sodium hydride → 7-(2-Methyl-4,5-diphenyl-imidazol-1-yl)-heptanoic acid ethyl ester

HRID 1351010Notes

Reaction equation

HRID 1351010 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C=O)C.C(OCC)C>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][N:6]1[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=[C:2]1[CH3:1])[CH3:32]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoateHCID 2366964,5-Diphenyl-2-methylimidazole

Product 1

HCID 599261267-(2-Methyl-4,5-diphenyl-imidazol-1-yl)-heptanoic acid ethyl esterYield 72%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

(Scheme 1, (B)) To a solution of 2-methyl-4,5-diphenyl-1H-imidazole (0.20 g, 0.85 mmol) in DMF (6 mL) was added NaH (60% in mineral oil, 0.038 g, 0.94 mmol). The resulting mixture was stirred at rt for 10 min. The stirring continued for 2 hours after addition of ethyl 7-bromoheptanoate (0.21 g, 0.90 mmol). The reaction mixture was diluted with diethyl ether (30 mL), washed by water, and then was dried over MgSO4. After filtration and concentration in vacuo, the residue was purified by flash chromatography (SiO2: EtOAc/Hexanes). This compound was obtained as a colorless oil (0.24 g, 0.61 mmol, 72% yield): 1H NMR (DMSO-d6) δ1.08 (m, 4H), 1.15 (t, J=7.2 Hz, 3H), 1.33 (m, 4H), 2.16 (t, J=6.6 Hz, 2H), 2.40 (s, 3H), 3.68 (t, J=7.8 Hz, 2H), 4.03 (q, J=4.5 Hz, 2H), 7.05)m, 1H), 7.13 (m, 2H), 7.34 (m, 4H), 7.48 (m, 3H); 13C NMR (DMSO-d6) δ13.4, 14.4, 24.3, 25.7, 27.8, 29.6, 33.5, 43.3, 59.9, 125.8, 126.0, 128.1, 128.3, 128.8, 129.3, 131.1, 131.8, 135.2, 135.3, and 144.0. Anal. Calcd for C25H30N2O2: C, 76.89; H, 7.74; N, 7.17. Found: C, 76.33; H, 7.67, N, 6.85.

Workup

  1. waitThe stirring continued for 2 hours
  2. washwashed by water
  3. dry with materialwas dried over MgSO4
  4. filtrationAfter filtration and concentration in vacuo
  5. customthe residue was purified by flash chromatography (SiO2: EtOAc/Hexanes)

Sources & evidence

ORD record
ord-6f63c7c6ebd54d8b82c554fcba4bd948
Source dataset
uspto-grants-2007_05
Patent number
USRE039634E1

Reaction notes

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