Hydrochloric Acid → 1-[(3,5-Difluoro-4-methoxyphenyl)methyl]-1,3-dihydro-2H-imidazole-2-thione

HRID 981574Notes

Reaction equation

HRID 981574 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([O:14][CH3:15])=[C:9]([F:16])[CH:8]=1.[S-:19][C:20]#[N:21].[K+].Cl>C(O)C.O>[F:16][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([F:13])[C:10]=1[O:14][CH3:15])[CH2:6][N:5]1[CH:4]=[CH:3][N:21]=[C:20]1[SH:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516872Potassium thiocyanateHCID 14450862N-(3,5-difluoro-4-methoxybenzyl)-aminoacetaldehyde dimethyl acetal

Product 1

HCID 144508631-[(3,5-Difluoro-4-methoxyphenyl)methyl]-1,3-dihydro-2H-imidazole-2-thioneYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-(3,5-difluoro-4-methoxybenzyl)-aminoacetaldehyde dimethyl acetal (4.94 g, 0.0189 mole) in ethyl alcohol (30 ml) was added potassium thiocyanate (2.10 g, 0.0216 mole) in water (48 ml) followed by 12 N hydrochloric acid (4 ml), and the reaction mixture was heated under reflux for 3.5 hours. The solvent was partially removed under reduced pressure, the mixture was cooled in ice, and the product was filtered. The product was recrystallized from ethyl alcohol - hexane to give 1-(3,5-difluoro-4-methoxybenzyl)-2-mercaptoimidazole as a solid melting at 160-161° (2.22 g, 46%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 3.5 hours
  3. customThe solvent was partially removed under reduced pressure
  4. temperaturethe mixture was cooled in ice
  5. filtrationthe product was filtered
  6. customThe product was recrystallized from ethyl alcohol - hexane

Sources & evidence

ORD record
ord-30c6c962bc5045ae888a1a2e949b0001
Source dataset
uspto-grants-1991_02
Patent number
US04992459

Reaction notes

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