Hydrochloric Acid → 1-[(1,3-Thiazol-2-yl)methyl]-1,3-dihydro-2H-imidazole-2-thione

HRID 1193569Notes

Reaction equation

HRID 1193569 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.C(O[CH:11](OCC)[CH2:12][NH2:13])C.CC1C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+].[C:30]([S-:32])#[N:31].[K+].Cl>C(O)C.O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:13]1[CH:12]=[CH:11][NH:31][C:30]1=[S:32]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 695242,2-DiethoxyethylamineHCID 516872Potassium thiocyanateHCID 27349031,3-Thiazole-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 212726181-[(1,3-Thiazol-2-yl)methyl]-1,3-dihydro-2H-imidazole-2-thione

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

In a 500 ml round bottom blask is placed 6 g (0.053 mol) 2-thiazolecarboxaldehyde, 7.0 g (0.053 mol) aminoacetaldehyde diethylacetal, 0.1 g TsOH and 150 ml ethanol. The reaction is refluxed 2 hours, cooled and concentrated. The residue is redissolved in 200 ml ethanol and 2.3 g (0.06 mol) NaBH4 added. The reaction is refluxed 4 hours then poured onto 500 ml water. The amino derivative is extracted into CH2Cl2 (2×100 ml), dried (Na2SO4) and concentrated to give an orange oil. The entire product is dissolved in 200 ml ethanol and 5.1 g (0.053 mol) KSCN, 30 ml water and 8 ml concentrated HCl added. The reaction is refluxed for 6 hours, cooled and then poured onto 1 liter ice water. The tan solid is collected and dried.

Workup

  1. temperatureThe reaction is refluxed 2 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. dissolutionThe residue is redissolved in 200 ml ethanol
  5. temperatureThe reaction is refluxed 4 hours
  6. extractionThe amino derivative is extracted into CH2Cl2 (2×100 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customto give an orange oil
  10. temperatureThe reaction is refluxed for 6 hours
  11. temperaturecooled
  12. customThe tan solid is collected
  13. customdried

Sources & evidence

ORD record
ord-0cbeebf686b54534aa6109a80dbc853f
Source dataset
uspto-grants-1989_03
Patent number
US04810800

Reaction notes

Loading…