Cyclohexyl isocyanate → HCID 9847217, compound

HRID 2101739Notes

Reaction equation

HRID 2101739 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[CH:11]=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.[Li]CCCC.[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]([CH3:13])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[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

A solution of 5.5 g (16.2 mmol) of 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-imidazole in 70 mL of THF was cooled in a −78° C. bath and 15 mL of 1.6 M n-BuLi was slowly added. After stirring for 1 h, 5.2 mL (40.7 mmol) of cyclohexylisocyanate was added. The cooling bath was removed and the solution was stirred for 3 h. The reaction mixture was poured into a mixture of water/EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried and concentrated. The residue was purified on a flash column using a gradient of 2-10% EtOAc-hexane. The isolated product was crystallized from EtOAc-hexane (˜1:10) to obtain the title compound as a white solid with a melting point of 165° C.

Workup

  1. customThe cooling bath was removed
  2. stirringthe solution was stirred for 3 h
  3. additionThe reaction mixture was poured into a mixture of water/EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washThe combined organic layer was washed with brine
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified on a flash column
  10. customThe isolated product was crystallized from EtOAc-hexane (˜1:10)

Sources & evidence

ORD record
ord-6dfc7870f5aa4984b9da6e669f9f465f
Source dataset
uspto-grants-2009_08
Patent number
US07572785B2

Reaction notes

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