Sulfuric Acid → 5,5-Bis(4-methylphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione

HRID 1248926Notes

Reaction equation

HRID 1248926 reaction equation
O.[NH:2]1[C:10](=[O:11])[C:8](=O)[C:6](=[O:7])[NH:5][C:3]1=[O:4].S(=O)(=O)(O)O.[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Hg]>[C:17]1([CH3:23])[CH:22]=[CH:21][C:20]([C:8]2([C:20]3[CH:21]=[CH:22][C:17]([CH3:23])=[CH:18][CH:19]=3)[C:10](=[O:11])[NH:2][C:3](=[O:4])[NH:5][C:6]2=[O:7])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 167232,4,5,6(1H,3H)-Pyrimidinetetrone, monohydrate

Product 1

HCID 133313275,5-Bis(4-methylphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione

Reagents, catalysts & solvents 1

HCID 23931MercuryCatalyst

Procedure

In a 500 cc. 3-necked flask fitted with a reflux condenser, a mercury seal stirrer and a thermometer in a well, were placed 16 g. of alloxan monohydrate and 60 g. of sulfuric acid, sp.gr. 1.84. Then 75 cc. of toluene were added through the reflux condenser and the mixture heated in an oil-bath, with stirring for four and one-half hours at 75°-80°. After this time the reaction mixture was cooled, most of the toluene later decanted, and the sirupy sulfuric acid later poured into 150 cc. of cold water. The precipitated material was filtered and washed in a beaker with 100 cc. of water and refiltered. After drying in a vacuum this material was dissolved in 160 cc. of boiling glacial acetic acid, filtered and allowed to crystallize.

Workup

  1. custom3-necked flask fitted with a reflux condenser
  2. temperaturethe mixture heated in an oil-bath
  3. customlater decanted
  4. additionthe sirupy sulfuric acid later poured into 150 cc
  5. filtrationThe precipitated material was filtered
  6. washwashed in a beaker with 100 cc
  7. customAfter drying in a vacuum this material
  8. dissolutionwas dissolved in 160 cc
  9. filtrationof boiling glacial acetic acid, filtered
  10. customto crystallize

Sources & evidence

ORD record
ord-b670f945beaa43008d1c6a1534eb0b64
Source dataset
uspto-grants-1986_12
Patent number
US04628056

Reaction notes

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