Triethylamine → 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-(1-methoxycyclohexyloxy)methyl-1H-imidazole

HRID 1005515Notes

Reaction equation

HRID 1005515 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][OH:17])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH+]1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:38][O:39][C:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH:41]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][O:17][C:40]3([O:39][CH3:38])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 702641-MethoxycyclohexeneHCID 473916(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanolHCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 187920075-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-(1-methoxycyclohexyloxy)methyl-1H-imidazoleYield 83.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-2-hydroxymethyl-1H-imidazole (14) (33 mg, 0.1 mmol) prepared in accordance with the method as described in WO 96/10019 and p-toluenesulfonic acid pyridinium (27.6 mg, 0.11 mmol) in toluene (1.5 mL) was added 1-methoxycyclohexene (112 mg, 1.00 mmol) under ice-cooling, and stirred at room temperature for 6 hours. A drop of triethylamine was added to the reaction mixture, and the mixture was filtered to remove the insoluble matter. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on an alumina column (eluate: toluene) to give the compound 15 (37.0 mg, 70%) as oil. Rf 0.16 (Al2O3 60, Type E, toluene).

Workup

  1. temperaturecooling
  2. filtrationthe mixture was filtered
  3. customto remove the insoluble matter
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by chromatography on an alumina column (eluate: toluene)

Sources & evidence

ORD record
ord-a286971f7e184e91b02b73dd4c884107
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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