Hydrochloric Acid → 1,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

HRID 1740486Notes

Reaction equation

HRID 1740486 reaction equation
[CH2:1]([N:8]1[C@H:12]2[CH2:13][O:14][C:15](=O)[C@H:11]2[N:10]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[S].[SH2:31].Cl>[Zn].O.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C@H:12]2[CH2:13][S:31][C:15](=[O:14])[C@H:11]2[N:10]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 402Hydrogen Sulfide2×HCID 119819(3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dioneHCID 517045Sodium AcetateHCID 5362487Sulfur

Product 1

HCID 1198171,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

After heating to 90° C. a mixture of 38.68 g of (+)-cis-1,3-dibenzylhexahydrofuro[3,4-d]imidazole-2,4-dione, 6.04 g of sodium acetate, 2.49 g of sulfur and 47.56 g of polyethylene glycol (the average molecular weight: 600), it was stirred for 4.5 hours at the temperature while blowing 4.50 g of hydrogen sulfide at a rate of 10 ml/minute. Then blowing of hydrogen sulfide was stopped and the resultant mixture was stirred for 5 hours at the temperature. After cooling the reaction mixture to room temperature, 173.61 g of toluene and 99.70 g of water were added to the mixture, and 8.25 g of zinc powder was further added to the mixture while stirring at room temperature. After dropping 54.90 g of 35% hydrochloric acid at the same temperature, the resultant mixture was stirred at 45° C. for 8 hours. The mixture was separated by removing water layer to give an oil layer, which was concentrated to give a product. Recrystallization from 2-propanol and water gave a crystal of (+)-cis-1,3-dibenzylhexahydrothieno[3,4-d]imidazole-2,4-dione. The yield was 36.96 g (yield percentage: 91%). Melting point was 126° C. [α]D20 was 90° C.=1.0; chloroform).

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. additionwas further added to the mixture
  3. stirringwhile stirring at room temperature
  4. customThe mixture was separated
  5. customby removing water layer
  6. customto give an oil layer, which
  7. concentrationwas concentrated
  8. customto give a product
  9. customRecrystallization from 2-propanol and water

Sources & evidence

ORD record
ord-81b21340cc9d40309052f93bc1ed2125
Source dataset
uspto-grants-1999_10
Patent number
US05969149

Reaction notes

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