Allylamine → HCID 18326474, compound

HRID 1250606Notes

Reaction equation

HRID 1250606 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].P(Cl)(Cl)(Cl)=O.C(N(C(C)C)C=O)(C)C.Cl.[F:31][C:32]([F:36])([F:35])[CH2:33][NH2:34].C(N(CC)CC)C.[CH2:44]([NH2:47])[CH:45]=[CH2:46]>O>[CH2:44]([NH:47][C:9]1[N:8]=[C:7]([NH:34][CH2:33][C:32]([F:36])([F:35])[F:31])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1)[CH:45]=[CH2:46]

Participants

8

Reactant 6

HCID 7853AllylamineHCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 24813Phosphorus oxychlorideHCID 75912N,N-bis(1-methylethyl)formamideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 18326474HCID 18326474, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 250 mg (1.21 mmol) of 6-nitroquinazoline-2,4(1H,3H)-dione were added 5.00 ml (53.64 mmol) of phosphorus oxychloride and 0.18 ml (1.21 mmol) of diisopropylformamide, and the resulting mixture was subjected to heating under reflux for 24 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 5 ml of acetonitrile, followed by addition of 328 mg (2.42 mmol) of 2,2,2-trifluoroethylamine hydrochloride and 1.69 ml (12.10 mmol) of triethylamine under ice cooling 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, 1.50 ml (20.00 mmol) of allylamine was added thereto, followed by stirring overnight, adding water to the reaction solution, 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 50 mg (12.6%) of the title compound.

Workup

  1. temperatureto heating
  2. temperatureunder reflux for 24 hours
  3. customAfter phosphorus oxychloride was removed in vacuo
  4. dissolutionthe mixture was dissolved in 5 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. stirringby stirring overnight
  10. extractionto the reaction solution, extraction with ethyl acetate
  11. washwashing with brine
  12. dry with materialdrying over anhydrous sodium sulfate
  13. distillationAfter the solvent was distilled off
  14. customthe residue was purified by a silica gel column

Sources & evidence

ORD record
ord-00f941b5b9464fa1b079ca3fff9a2cfa
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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