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

HRID 597596Notes

Reaction equation

HRID 597596 reaction equation
[CH2:1]([N:8]1[C@H:12]([CH2:13][OH:14])[C@H:11]([C:15](=[O:32])NC(C2C=CC=CC=2)CC2C=CC(C)=CC=2)[N:10]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:9]1=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>O1CCOCC1>[CH2:1]([N:8]1[C@H:12]2[CH2:13][O:14][C:15](=[O:32])[C@H:11]2[N:10]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:9]1=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 70637872HCID 70637872, compound

Product 1

HCID 119819(3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dioneYield 84.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the amide-alcohol (3.0 g) prepared in Example 8, dioxane (30 ml) and 20 % sulfuric acid (20 ml) is refluxed with stirring for 1 hour. After the reaction is completed, the mixture is concentrated to one third of the original volume and diluted with water (50 ml). The precipitate is filtered to give cis-1,3-dibenzyl-hexahydrofuro[3,4-d]imidazole-2,4-dione (1.53 g, 84.5 %). M.P. 106.5° to 109° C. [α]D20 + 2.6° (C = 2 in CHCl3). The infrared spectrum of the sample is identified with that of the authentic sample.

Workup

  1. temperatureis refluxed
  2. concentrationthe mixture is concentrated to one third of the original volume
  3. additiondiluted with water (50 ml)
  4. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-3844470204344542bf5babf1a40b3777
Source dataset
uspto-grants-1977_03
Patent number
US04014895

Reaction notes

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