Pyridine → 2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1 H-imidazole-4-carboxylic acid [7-(2-amino-ethoxyimino)-7-[4-(trifluoromethyl)phenyl] heptyl]-amide

HRID 1095438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095438
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([C:19]2[N:20]=[C:21]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])[N:22]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:23]=2[CH2:24][CH3:25])=[O:18])=[CH:5][CH:4]=1.Cl.Cl.[NH2:45][CH2:46][CH2:47][O:48][NH2:49].N1C=CC=CC=1>C(O)C>[NH2:45][CH2:46][CH2:47][O:48][N:49]=[C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:41])([F:1])[F:42])=[CH:4][CH:5]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([C:19]1[N:20]=[C:21]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:39])[N:22]([C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)[C:23]=1[CH2:24][CH3:25])=[O:18]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 143623262-(O-aminooxy)ethylamine dihydrochlorideHCID 667841402-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1H-imidazole-4-carboxylic acid {7-[4-(trifluoromethyl)phenyl]-7-oxo-heptyl}amide

Produkt 1

HCID 866229112-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1 H-imidazole-4-carboxylic acid [7-(2-amino-ethoxyimino)-7-[4-(trifluoromethyl)phenyl] heptyl]-amideAusbeute 106,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Part C: 2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1H-imidazole-4-carboxylic acid {7-[4-(trifluoromethyl)phenyl]-7-oxo-heptyl}amide (1.15 g, 1.86 mmol) was dissolved in absolute ethanol (10 ml), and O-(2-aminoethyl)hydroxylamine dihydrochloride (0.276 mg, 1.865 mol) and pyridine (0.18 ml) were successively added. The resulting mixture was stirred at reflux temperature for 20 hours. The mixture was allowed to attain room temperature. After removal of the solvent in vacuo, the residue was dissolved in dichloromethane and washed successively with an aqueous KHSO4 solution and brine. The organic layer was subsequently dried over Na2SO4, filtered and concentrated in vacuo to give 2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1 H-imidazole-4-carboxylic acid [7-(2-amino-ethoxyimino)-7-[4-(trifluoromethyl)phenyl] heptyl]-amide (Compound 2) (1.34 g) as a mixture of E/Z stereoisomers. Melting point: 90-95° C. 1H-NMR (400 MHz, CDCl3) δ 1.05 (t, J=7, 3H), 1.34-1.62 (m, 8H), 2.81 (br t, J=7, 2H), 2.93 (q, J=7, 2H), 3.32-3.42 (m, 4H), 4.44-4.50 (m, 2H), 7.11 (d, J=8, 2H), 7.21-7.34 (m, 5H), 7.37 (d, J=8, 1H), 7.49 (br s, 1H), 7.59 (d, J=8, 2H), 7.71 (d, J=8, 2H), 8.65 (br s, 2H).

Aufarbeitung

  1. temperatureat reflux temperature for 20 hours
  2. customto attain room temperature
  3. customAfter removal of the solvent in vacuo
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed successively with an aqueous KHSO4 solution and brine
  6. dry with materialThe organic layer was subsequently dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-25fe281254bf41469733d16c376a11cd
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138174B2

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