Sulfuric Acid → HCID 53778393, compound

HRID 1106284Notes

Reaction equation

HRID 1106284 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=O)C.O.[C:15]([OH:19])(=[O:18])[CH:16]=O.OS(O)(=O)=O.[O:25]1[CH2:30][CH2:29]OCC1>O>[NH2:13][S:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:1][C:30](=[O:25])[CH:29]=[CH:16][C:15]([OH:19])=[O:18])=[CH:5][CH:6]=1)(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 740654-AcetylbenzenesulphonamideHCID 15620607Glyoxylic acid, monohydrate2×

Product 1

HCID 53778393HCID 53778393, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 37 g of p-acetylbenzenesulfonamide, 78.4 g of glyoxylic acid hydrate, 20 ml of 80% H2SO4 and 180 ml of dioxane is refluxed for 24 hours. An additional 10 g of glyoxylic acid hydrate is added and the mixture is refluxed for 24 hours. The reaction mixture is poured into 2 liters of water and extracted with ether. The organic layers are combined, dried, and evaporated to leave a solid which is crystallized from acetonitrile yielding 10.9 g of the title compound, melting point 180°-181° C.

Workup

  1. temperatureis refluxed for 24 hours
  2. temperaturethe mixture is refluxed for 24 hours
  3. extractionextracted with ether
  4. customdried
  5. customevaporated
  6. customto leave a solid which
  7. customis crystallized from acetonitrile yielding 10.9 g of the title compound, melting point 180°-181° C.

Sources & evidence

ORD record
ord-8f5b4e3dcabe4666b42b5aa22fe64daf
Source dataset
uspto-grants-1982_01
Patent number
US04312990

Reaction notes

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