Dichloromethane methanol → HCID 178425336, compound

HRID 1416025Notes

Reaction equation

HRID 1416025 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][C:13]([CH3:15])=[N:12][CH:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH3:16][OH:17].C(Cl)Cl>>[CH3:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[NH:14][C:13]([CH3:15])=[N:12][C:11]=2[CH2:16][OH:17])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

3

Reactant 2

HCID 21226129Dichloromethane methanolHCID 22131032HCID 22131032, compound

Product 1

HCID 178425336HCID 178425336, compoundYield 21%

Procedure

Heated was a solution of 7.0 g (3.2 mmol)of 5-(3,5-dimethylphenylthio)-2-methyl-1H-imidazole (5b)in 37% aqueous formaline (20 ml)at 120° C. for 15 hours in a sealed tube. The reaction mixture was dissolved in methanol/methylene chloride, and the aqueous layer was separated off. The organic layer was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (methanol:ethyl acetate=2:98), and the crude product was washed with isopropyl ether to obtain 1.7 g of [5-(3,5-dimethylphenylthio)-2-methyl-1H-imidazol-4-yl]methanol (41d)(yield 21%). mp 199-201° C.

Workup

  1. temperatureHeated
  2. customat 120° C.
  3. customfor 15 hours
  4. customthe aqueous layer was separated off
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography (methanol:ethyl acetate=2:98)
  8. washthe crude product was washed with isopropyl ether

Sources & evidence

ORD record
ord-51cc42479aba4bea8263511ef3fa1406
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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