Formaldehyde → HCID 178425336, compound

HRID 1857724Notes

Reaction equation

HRID 1857724 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.[CH2:16]=[O:17]>CO.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

4

Reactant 2

HCID 712FormaldehydeHCID 22131032HCID 22131032, compound

Product 1

HCID 178425336HCID 178425336, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

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-929a6aded4dd4e39a103be3c6b4f1f8e
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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