Hydrochloric Acid → HCID 178490797, compound

HRID 981567Notes

Reaction equation

HRID 981567 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]=O)=[CH:7][CH:8]=1.C(O[CH:14](OCC)[CH2:15][NH2:16])C.[C:20]([S-:22])#[N:21].[K+].Cl>C(O)C.[Pd].O.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][N:16]2[CH:15]=[CH:14][N:21]=[C:20]2[SH:22])=[CH:7][CH:8]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 312444-MethoxybenzaldehydeHCID 695242,2-DiethoxyethylamineHCID 516872Potassium thiocyanate

Product 1

HCID 178490797HCID 178490797, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 13.6 g (0.1 mole) of anisaldehyde, 3.3 g (0.1 mole) of aminoacetaldehyde diethyl acetal and ml of CH3OH was heated at 95° for 10 minutes. A residue was dissolved in 150 ml of ethanol and hydrogenated over 10% Pd on carbon at 50 psi (0.34 MPa) until H2 uptake was complete. The catalyst was filtered and the filtrate was treated with 10.4 g (0.107 mole) of KSCN, 0 ml of 3N HCl and 40 ml of H2O. The mixture was refluxed, letting the solvent evaporate until the volume of the reaction mixture was 100 ml. After 45 minutes, the mixture was cooled, and a solid was filtered, washed with H2O and dried. Recrystallization from ethanol gave (1-(4-methoxybenzyl)-2-mercaptoimidazole, 15.0 g (68%), mp 140-142°.

Workup

  1. temperaturewas heated at 95° for 10 minutes
  2. filtrationThe catalyst was filtered
  3. temperatureThe mixture was refluxed
  4. customevaporate until the volume of the reaction mixture
  5. temperaturethe mixture was cooled
  6. filtrationa solid was filtered
  7. washwashed with H2O
  8. customdried
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-10f9505a4f804611a44c675da5ca5c1d
Source dataset
uspto-grants-1991_02
Patent number
US04992459

Reaction notes

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