Cyclohexyl isocyanate → HCID 9847217, compound

HRID 2101723Notes

Reaction equation

HRID 2101723 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[CH:11][N:12]([CH3:21])[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=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:11]2[N:12]([CH3:21])[C:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[N:10]=2)=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 18502Cyclohexyl isocyanateHCID 22066095HCID 22066095, compoundHCID 178418339Butyllithium

Product 1

HCID 9847217HCID 9847217, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-1-methylimidazole (50 mg, 0.15 mmol) from Example 32, Step C (lower Rf isomer) in THF (2.5 mL) cooled to −70° C. in a dry ice/acetone bath was added 1.6N n-butyl lithium in hexanes (0.120 mL, 0.18 mmol). The reaction was stirred for 1 hr and then cyclohexyl isocyanate (0.040 mL, 0.30 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 (2×1 mm, silica) (25% ethyl acetate in hexanes) to afford the title compound.

Workup

  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 (2×1 mm, silica) (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-189fa743b05f4deaacadab5e1a55bf1c
Source dataset
uspto-grants-2009_08
Patent number
US07572785B2

Reaction notes

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