Hydrochloric Acid → HCID 178527873, compound

HRID 579756Notes

Reaction equation

HRID 579756 reaction equation
CO[CH:3](OC)[CH2:4][NH2:5].[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=O.[BH4-].[Na+].[S-:17][C:18]#[N:19].[K+].Cl>C(O)C.O>[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][N:5]1[CH:4]=[CH:3][N:19]=[C:18]1[SH:17]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 73642-ThiophenecarboxaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 516872Potassium thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 178527873HCID 178527873, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of aminoacetaldehyde dimethylacetal (5.45 ml., 0.05 mole) and 2-thiophenecarboxaldehyde (4.67 ml., 0.05 mole) was heated at 100° C. for 2 hours and the reaction mixture was cooled in ice and diluted with ethyl alcohol (50 ml.). Sodium borohydride (1 g) was added to the solution and the reaction mixture was stirred for 17 hours. The solvent was removed under vacuum, ethyl acetate (50ml) was added, and the solution was washed with water and brine and dried over sodium sulfate. The mixture was filtered and the solvent was removed under vacuum. The resultant oil was diluted with ethyl alcohol (69 ml), potassium thiocyanate (5.59 g, 0.0575 mole) in water (115 ml) followed by concentrated hydrochloric acid (11.5 ml) and the solution was heated at reflux for 2.5 hours. The solvent was removed until an oil came out of solution at which point the reaction mixture was cooled with ice, diluted with water, and the crude product was filtered. The product was first recrystallized from a mixture of ethyl acetate-hexane followed by ethyl acetate to give 1-(2-thienylmethyl)imidazole-2-thiol, melting at 130°-131° C. (2.79 g., 28%).

Workup

  1. temperaturethe reaction mixture was cooled in ice
  2. customThe solvent was removed under vacuum, ethyl acetate (50ml)
  3. additionwas added
  4. washthe solution was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe mixture was filtered
  7. customthe solvent was removed under vacuum
  8. temperaturethe solution was heated
  9. temperatureat reflux for 2.5 hours
  10. customThe solvent was removed until an oil
  11. temperaturewas cooled with ice
  12. additiondiluted with water
  13. filtrationthe crude product was filtered
  14. customThe product was first recrystallized from a mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-ff540697699944748cab8f89dd34fb9b
Source dataset
uspto-grants-1988_06
Patent number
US04749717

Reaction notes

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