Dimethylformamide → HCID 10487222, compound

HRID 268329Notes

Reaction equation

HRID 268329 reaction equation
C([C:4]1[CH:12]=[N:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(=O)N.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].C[N:31](C)[CH:32]=[O:33]>>[C:5]12[C:4](=[CH:12][N:11]=[CH:10][CH:9]=1)[NH:31][C:32](=[O:33])[O:8][C:6]2=[O:7]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 21551406HCID 21551406, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 10487222HCID 10487222, compound

Procedure

A 50 ml. flask was charged with 0.94 g. 3-carbamylisonicotinic acid suspended in 8 ml. dimethylformamide. A 2.5 g. portion of lead tetra-acetate was added to the suspension, and the reaction mixture was stirred at 20° for 10 minutes. The reaction mixture was then warmed to 45° and stirred for 10 minutes. The cooled mixture was poured onto 30 grams crushed ice and the pale yellow solids were collected by filtration and dried in vacuo. Extensive decomposition of the product occurred upon attempted recrystallization from organic solvents. The final yield of 4-azaisatoic anhydride amounted to 0.65 g., melting point 218°, with decomposition, and represented 70 percent of theory. The structure was identified by elemental analysis, infrared spectroscopy and mass spectrometry.

Workup

  1. additionflask was charged with 0.94 g
  2. temperatureThe reaction mixture was then warmed to 45°
  3. stirringstirred for 10 minutes
  4. additionThe cooled mixture was poured onto 30 grams
  5. customcrushed ice
  6. filtrationthe pale yellow solids were collected by filtration
  7. customdried in vacuo
  8. customrecrystallization from organic solvents

Sources & evidence

ORD record
ord-925ed670a95d47608fc5875d10396efd
Source dataset
uspto-grants-1976_03
Patent number
US03947442

Reaction notes

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