Cyclohexyl isocyanate → N-(Cyclohexyl)-4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-1-methylimidazole-2-carboxamide

HRID 1828593

Reaktionsgleichung

Reaktionsgleichung von HRID 1828593
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH3:21])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=[CH:4][CH:3]=1.C([Li])CCC.[CH:27]1([N:33]=[C:34]=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C1COCC1>[CH:27]1([NH:33][C:34]([C:10]2[N:11]([CH3:21])[C:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]=2)=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Komponenten

5

Edukt 3

HCID 18502Cyclohexyl isocyanateHCID 220660834-(4-Chlorophenyl)-5-(2,4-dichlorophenyl)-1-methylimidazoleHCID 178418339Butyllithium

Produkt 1

HCID 10204999N-(Cyclohexyl)-4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-1-methylimidazole-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-1-methylimidazole (50 mg, 0.15 mmol) from Example 32, Step C in THF (3 mL) cooled to −70° C. in a dry ice/acetone bath was added 1.6N n-butyl lithium in hexanes (0.11 mL, 0.18 mmol). The reaction was stirred for 1 hr and then cyclohexyl isocyanate (0.040 mL, 30 mmol) was added via syringe. The reaction was allowed to warm to rt for 1 hr and was then quenched with aq. sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by Prep TLC (1 mm, silica) (100% methylene chloride) to afford the title compound.

Aufarbeitung

  1. customwas then quenched with aq. sodium bicarbonate
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by Prep TLC (1 mm, silica) (100% methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-e9a99b1ec7404786be72cf026a3b34fa
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07057051B2

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