Benzylamine → HCID 11056142, compound

HRID 2258429Notes

Reaction equation

HRID 2258429 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C.[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[CH2:28]([NH:35][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([N+:13]([O-:15])=[O:14])[CH:4]=2)[N:9]=[CH:8][N:7]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1356875047-Chloro-6-nitroquinazolin-4(1H)-one

Product 1

HCID 11056142HCID 11056142, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-Chloro-6-nitro-4(3H)-quinazolone [J. Org. Chem., 40, 356 (1975) etc.] (10 g, 54.8 mmol) was added to phosphorus oxychloride (40 ml) under ice-cooling. A temperature of the mixture was gradually raised and the mixture was refluxed for 2 hours. After evaporation of the solvent under reduced pressure, a solution of triethylamine (200 ml, 1.43 mol) and benzylamine (40 ml, 366 mmol) dissolved in tetrahydrofuran (500 ml) was added to the residue under ice-cooling. A temperature of the mixture was raised to room temperature and the mixture was stirred overnight. After evaporation of the solvent under reduced pressure, water and chloroform were added and the organic layer was separated. The aqueous layer was extracted with chloroform and the chloroform layer was combined with the organic layer. The combined organic layer was washed with water and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, a mixed solvent of methanol and water was added thereto. The precipitated crystals were filtered off to give the title compound (8.55 g, 49.6%).

Workup

  1. temperaturecooling
  2. temperatureA temperature of the mixture was gradually raised
  3. temperaturethe mixture was refluxed for 2 hours
  4. customAfter evaporation of the solvent under reduced pressure
  5. additionwas added to the residue under ice-
  6. temperaturecooling
  7. customAfter evaporation of the solvent under reduced pressure, water and chloroform
  8. additionwere added
  9. customthe organic layer was separated
  10. extractionThe aqueous layer was extracted with chloroform
  11. washThe combined organic layer was washed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customAfter evaporation of the solvent under reduced pressure
  14. additiona mixed solvent of methanol and water was added
  15. filtrationThe precipitated crystals were filtered off

Sources & evidence

ORD record
ord-a4363f251b1f419a8d84393d0a85537c
Source dataset
uspto-grants-1997_08
Patent number
US05661147

Reaction notes

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