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

HRID 2057126Notes

Reaction equation

HRID 2057126 reaction equation
[CH2:1]([N:8]1[C@H:12]2[CH2:13][S:14][C:15](=[O:16])[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.N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C@H:12]2[CH2:13][S:14][C:15](=[O:16])[C@H:11]2[N:10]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 86596559(3aR,6aR)-1,3-dibenzyl-hexahydro-4H-thieno[3,4-d]imidazol-2,4-dione

Product 1

HCID 1198171,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dioneYield 75.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 1 ml of chloroform was dissolved 100 mg of (3aR,6aR)-1,3-dibenzyl-hexahydro-4H-thieno[3,4-d]imidazol-2,4-dione, 0.5 ml of pyridine was added to the solution, and the resulting mixture was stirred at room temperature for 23 hours. The reaction mixture was successively washed with 2M hydrochloric acid, water, a saturated sodium bicarbonate solution, and saturated brine. The organic layer was dried and then concentrated. By adding isopropyl ether, precipitated crystal was collected by filtration to give 75.1 mg of (3aS,6aR)-1,3-dibenzyl-hexahydro-4H-thieno[3,4-d]imidazol-2,4-dione.

Workup

  1. additionwas added to the solution
  2. washThe reaction mixture was successively washed with 2M hydrochloric acid, water
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. additionBy adding isopropyl ether
  6. customprecipitated crystal
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-8321c2ea62d149cb820b1f7438810940
Source dataset
uspto-grants-2008_02
Patent number
US07335778B2

Reaction notes

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