1,1-Dimethylhydrazine → HCID 18326472, compound

HRID 1250597Notes

Reaction equation

HRID 1250597 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.[CH3:29][N:30]([CH3:32])[NH2:31]>O>[Cl:26][C:9]1[N:8]=[C:7]([NH:31][N:30]([CH3:32])[CH3:29])[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 59761,1-DimethylhydrazineHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 24813Phosphorus oxychlorideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 18326472HCID 18326472, compound

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 1.23 g (8.05 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 520 mg (8.69 mmol) of N,N-dimethylhydrazine 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 to give 2-chloro-4-(2,2-dimethylhydrazino)-6-nitroquinazoline. After 2.00 ml (26.65 mmol) of allylamine was added thereto and then the mixture was stirred at room temperature for 3 hours, water was added to the reaction solution, 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 73 mg (17.5%) of the title compound.

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

Sources & evidence

ORD record
ord-784c7475af9548e391af77f290d69c49
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

Loading…