Alloxan → 1,2,3,4-Tetrahydrobenzopteridine-2,4-dione

HRID 2413320Notes

Reaction equation

HRID 2413320 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[NH:9]1[C:17](=O)[C:15](=O)[C:13](=[O:14])[NH:12][C:10]1=[O:11]>O>[CH:4]1[CH:5]=[CH:6][C:1]2[C:2](=[N:7][C:15]3[C:13](=[O:14])[NH:12][C:10](=[O:11])[NH:9][C:17]=3[N:8]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 5781AlloxanHCID 7243O-Phenylenediamine

Product 1

HCID 53727201,2,3,4-Tetrahydrobenzopteridine-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

There was charged 800 ml of water into an Erlenmeyer flask, then 3.5 g (30 mmoles) of o-phenylenediamine and 5.0 g (30 mmoles) of alloxan were added thereto, and the mixture was stirred at room temperature in a nitrogen atmosphere for about 5 hours. The obtained reaction mixture was cooled with ice for 3 hours, then the formed yellow precipitate was filtered off, and washed in ethanol and ether (50 ml, twice). This precipitate was recrystallized from an aqueous dimethylformamide solution to give pale yellow powdery crystals. Yield: 7.5 g (90%). M.p. 300° C. or higher. IR spectrum: Found values (cm-1): 1730, 1705 (C=O stretching), 1572 (Broad peak) --C=N (amide II band). Literature values (cm-1): 1727, 1700, 1574.

Workup

  1. customThe obtained reaction mixture
  2. temperaturewas cooled with ice for 3 hours
  3. filtrationthe formed yellow precipitate was filtered off
  4. washwashed in ethanol
  5. customThis precipitate was recrystallized from an aqueous dimethylformamide solution
  6. customto give pale yellow powdery crystals

Sources & evidence

ORD record
ord-97d95692c4944e929ff023ee775a4fa8
Source dataset
uspto-grants-1985_01
Patent number
US04496646

Reaction notes

Loading…