Toluene → 5-(3,5-Dimethylphenylthio)-4-isopropyl-1-[2-(1-methoxycyclopentyloxy)ethoxymethyl]-2-methyl-1H-imidazole

HRID 1005504

Reaction equation

HRID 1005504 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][O:16][CH2:17][CH2:18][OH:19])[C:13]([CH3:20])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([CH3:8])[CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.[CH3:43][O:44][C:45]1[CH2:49][CH2:48][CH2:47][CH:46]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH2:15][O:16][CH2:17][CH2:18][O:19][C:45]3([O:44][CH3:43])[CH2:49][CH2:48][CH2:47][CH2:46]3)[C:13]([CH3:20])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 1368351-MethoxycyclopenteneHCID 4781802-[5-(3,5-Dimethyl-phenylsulfanyl)-4-isopropyl-2-methyl-imidazol-1-ylmethoxy]-ethanolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 158871845-(3,5-Dimethylphenylthio)-4-isopropyl-1-[2-(1-methoxycyclopentyloxy)ethoxymethyl]-2-methyl-1H-imidazoleYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of the compound 1 (33.4 mg, 0.1 mmol) and p-toluenesulfonic acid hydrate (20.4 mg, 0.108 mmol) in a mixture of methylene chloride (1 mL) -toluene (0.1 mL) was concentrated under reduced pressure. Trhe obtained residue was dissolved in methylene chloride (1 mL), to which was added 1-methoxycyclopentene (98.5 mg, 1 mmol), and the mixture was stirred for 2 hours. Triethylamine was added to the reaction mixture, and the mixture was concentrated under reduced pressure. The residue was purified by chromatography on an alumina column (eluate: hexane - ethyl acetate (2:1)) to give the same compound 2 (35 mg, 81 %) as the Example 1.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customTrhe obtained residue
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was purified by chromatography on an alumina column (eluate: hexane - ethyl acetate (2:1))

Sources & evidence

ORD record
ord-58c3d984846e47e9a72096e01ed8c5c1
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Linked notes

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