Benzene → HCID 20225640, compound

HRID 1248925Notes

Reaction equation

HRID 1248925 reaction equation
O.[CH3:2][N:3]1[C:11](=[O:12])[C:9](=O)[C:7](=[O:8])[N:6]([CH3:13])[C:4]1=[O:5].S(=O)(=O)(O)O.[CH:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[Hg]>[CH3:13][N:6]1[C:7](=[O:8])[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11](=[O:12])[N:3]([CH3:2])[C:4]1=[O:5]

Participants

5

Reactant 3

HCID 241Benzene2×HCID 1118Sulfuric AcidHCID 20225638HCID 20225638, compound

Product 1

HCID 20225640HCID 20225640, compound

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 18 g. of 1,3-dimethylalloxan monohydrate and 60 g. of sulfuric acid, sp. gr. 1.84. Then 75 cc. of benzene 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 benzene layer decanted, and the sirupy sulfuric acid layer 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 chromatographed on silica to furnish the pure product.

Workup

  1. custom3-necked flask fitted with a reflux condenser
  2. temperaturethe mixture heated in an oil-bath
  3. customdecanted
  4. additionthe sirupy sulfuric acid layer 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. customwas chromatographed on silica
  9. customto furnish the pure product

Sources & evidence

ORD record
ord-3dc7d0be20104e32b81b3cd50cb95c83
Source dataset
uspto-grants-1986_12
Patent number
US04628056

Reaction notes

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