1,3-Dimethyl-2-imidazolidinone → HCID 18326491, compound

HRID 1250578Notes

Reaction equation

HRID 1250578 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].CN1CCN(C)C1=O.P(Cl)(Cl)([Cl:26])=O.[CH2:29]([NH2:36])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>O>[Cl:26][C:9]1[N:8]=[C:7]([NH:36][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Participants

6

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 81271-HeptanamineHCID 24813Phosphorus oxychlorideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 18326491HCID 18326491, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 300 mg (1.45 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione were added 1 ml of 1,3-dimethyl-2-imidazolidinone and 2.22 g (14.48 mmol) of phosphorus oxychloride, and the resulting mixture was subjected to heating under reflux for 3 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 3 ml of acetonitrile, followed by addition of 5.38 ml (36.25 mmol) of heptylamine and stirring under ice cooling for 30 minutes. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 247 mg (yield: 52.8%) of the title compound (yield: 52.8%).

Workup

  1. temperatureto heating
  2. temperatureunder reflux for 3 hours
  3. customAfter phosphorus oxychloride was removed in vacuo
  4. dissolutionthe mixture was dissolved in 3 ml of acetonitrile
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashing with brine
  7. dry with materialdrying over anhydrous sodium sulfate
  8. distillationAfter the solvent was distilled off
  9. customthe residue was purified by a silica gel column

Sources & evidence

ORD record
ord-daa80190b3c44b538a72367dc92196e4
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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