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 653907Notes

Reaction equation

HRID 653907 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-4yl)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-1ba8795f225c4a80b79f7a40ea3faf8c
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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