Sulfuric Acid → (3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dione

HRID 597598Notes

Reaction equation

HRID 597598 reaction equation
[CH2:1]([N:8]1[C@H:12](O)[C@H:11]([C:14](=[O:23])NC(C2SC=CC=2)C)[N:10]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[O:37]1CCOC[CH2:38]1>>[CH2:1]([N:8]1[C@H:12]2[CH2:38][O:37][C:14](=[O:23])[C@H:11]2[N:10]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:9]1=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 68126015HCID 68126015, compound

Product 1

HCID 119819(3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dioneYield 95%

Procedure

A mixture of the amide-alcohol (2.0 g) prepared in Example 15, dioxane (50 ml) and 20 % sulfuric acid (30.0 g) is refluxed with stirring at 88° to 89° C for 1 hour. The reaction mixture is concentrated to one third of the original volume, diluted with water (50 ml) and cooled in an ice bath. The precipitate is collected by filtration to yield cis-1,3-dibenzyl-hexahyrofuro[3,4-d]imidazole-2,4-dione (1.36 g, 95 %). M.P. 100° to 103° C. [α]D20 + 16.4° (C = 2 in CHCl3). The infrared spectrum of the sample is identified with that of the authentic sample.

Workup

  1. temperatureis refluxed
  2. concentrationThe reaction mixture is concentrated to one third of the original volume
  3. additiondiluted with water (50 ml)
  4. temperaturecooled in an ice bath
  5. filtrationThe precipitate is collected by filtration

Sources & evidence

ORD record
ord-2bb52cb7db1b4357a4ccfdd3e55ea77d
Source dataset
uspto-grants-1977_03
Patent number
US04014895

Reaction notes

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