Dimethylformamide → 3-Methyl-1,2,3,4-tetrahydroquinazoline-2,4-dione

HRID 268332Notes

Reaction equation

HRID 268332 reaction equation
C[NH:2][C:3](=O)[C:4]1C(=C[CH:10]=[CH:11][CH:12]=1)C(N)=O.C[N:15]([CH3:18])[CH:16]=[O:17].[C:19]([O-:22])(=O)[CH3:20].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>O>[CH3:18][N:15]1[C:19](=[O:22])[C:20]2[C:3](=[CH:4][CH:12]=[CH:11][CH:10]=2)[NH:2][C:16]1=[O:17]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 21551410HCID 21551410, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 3443853-Methyl-1,2,3,4-tetrahydroquinazoline-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50 ml. flask was charged with 1.0 g. N-methylphthalamide suspended in 11 ml. dimethylformamide. A 2.6 g. portion of lead tetra-acetate was added to the suspension, and the reaction mixture stirred at 40°-50° for 2 hours. The reaction mixture was diluted with 15 ml. water, cooled and filtered. The yield amounted to 0.89 g., melting point 230°-232°, representing 88 percent of theory based on the N-methylphthalamide. The structure was confirmed by infrared spectroscopy.

Workup

  1. additionflask was charged with 1.0 g
  2. additionThe reaction mixture was diluted with 15 ml
  3. filtrationfiltered

Sources & evidence

ORD record
ord-f180bd543f82412e98b8e8689a11f442
Source dataset
uspto-grants-1976_03
Patent number
US03947442

Reaction notes

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