1-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-(2-methoxyethoxymethoxymethyl)imidazole → 1-[(2'-Carboxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-(2-methoxyethoxymethoxymethyl)imidazole

HRID 466424Notes

Reaction equation

HRID 466424 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:22]([CH2:23][O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])=[C:21]([Cl:31])[N:20]=[C:19]2[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:13][CH:12]=1)([O:3]C)=[O:2].C[S-].[K+]>CN(C)C=O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:22]([CH2:23][O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])=[C:21]([Cl:31])[N:20]=[C:19]2[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:13][CH:12]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 156980881-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-(2-methoxyethoxymethoxymethyl)imidazoleHCID 23693077Potassium Methanethiolate

Product 1

HCID 156980891-[(2'-Carboxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-(2-methoxyethoxymethoxymethyl)imidazoleYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.15 g of 1-[(2'-carbomethoxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-(2-methoxyethoxymethoxymethyl)imidazole and 2.77 g of potassium methanethiolate in 125 mL of dimethylformamide was stirred at 125° for 4 hours. After cooling the solvent was removed in vacuo, and the residue was dissolved in water. The resulting aqueous solution was washed with diethyl ether, adjusted to pH 3 employing 10% hydrochloric acid, and extracted with methylene chloride. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was recrystallized from chlorobutane to afford 2.45 g of 1-[(2'-carboxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-(2-methoxyethoxymethoxymethyl)imidazole. NMR (200 MHz, CDCl3) δ 7.95 (d, 1H); 7.57 (t, 1H); 7.46 (t, 1H); 7.38 (m, 3H); 7.05 (d, 2H); 5.22 (s, 2H); 4.64 (s, 2H); 4.48 (s, 2H); 3.58 (m, 4H); 3.40 (s, 3H); 2.54 (t, 2H); 1.60 (quint., 2H); 1.32 (sext., 2H); 0.84 (t, 3H).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas removed in vacuo
  3. dissolutionthe residue was dissolved in water
  4. washThe resulting aqueous solution was washed with diethyl ether
  5. extractionextracted with methylene chloride
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was recrystallized from chlorobutane

Sources & evidence

ORD record
ord-b0d3e24f729142bea1a338a840b38820
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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