Benzene → HCID 69747301, compound

HRID 1062450Notes

Reaction equation

HRID 1062450 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:10]=[C:11]([C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[OH:22])=[O:14])[N:12]=1.[CH:30]1C=CC=CC=1.[OH-].[Na+].CI>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.O.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[CH:10]=[C:11]([C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]2[O:22][CH3:30])=[O:14])[N:12]=1

Participants

8

Reactant 4

HCID 241BenzeneHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 23398425HCID 23398425, compound

Product 1

HCID 69747301HCID 69747301, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
10 °C

Procedure

A flask was charged with 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-[trans-2-hydroxycyclohexyl]-1H-imidazole-4-carboxamide (Table entry 336) (35 mg, 0.1 mmol), benzene (3 mL), 50% aqueous NaOH (2.5 mL), and Bu4NHSO4 (17 mg). While the mixture was stirred vigorously at 10° C., CH3I (19 μL, 0.3 mmol) was added dropwise rapidly. The mixture was stirred for another 30 minutes, and diluted with water (5 mL) and hexane (10 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (75% EtOAc in hexane) to give the product 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-[(1R,2S)-2-methoxycyclohexyl]-1H-imidazole-4-carboxamide (23 mg, 63% yield): LC-MS m/z 444.2 (MH+), retention time 3.24 min (method 1).

Workup

  1. stirringThe mixture was stirred for another 30 minutes
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (75% EtOAc in hexane)

Sources & evidence

ORD record
ord-21bef1ace94b44d5afc18c7254ceaaf1
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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