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 465815ノート

反応式

HRID 465815 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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) δ7.95 (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).

後処理

  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

出典と根拠

ORDレコード
ord-c24081b5c95f4a3aa5b66bd5f8bd1950
出典データセット
uspto-grants-1992_10
特許番号
US05153197

反応ノート

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