Aniline → 6-iodo-N-phenylquinazolin-4-amine

HRID 1881670Notes

Reaction equation

HRID 1881670 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=O.P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O.C1(C)C=CC=CC=1>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1354016666-Iodoquinazolin-4-one

Product 1

HCID 7248406-iodo-N-phenylquinazolin-4-amineYield 74.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

In a 20 mL-volume glass vessel equipped with a stirrer, a thermometer and a reflux condenser were placed 2.00 g (7.35 mmol) of 6-iodoquinazolin-4-one, 1.35 g (8.8 mmol) of phosphorus oxychloride, and 6 mL of toluene in a nitrogen atmosphere. While the mixture was stirred at room temperature, 0.89 g (8.8 mmol) of triethylamine was slowly added. The resulting mixture was heated to 75° C., and then reaction was carried out for 2 hours. Subsequently, the mixture was cooled to room temperature, and 3 mL of acetone and 821 mg (8.8 mmol) of aniline were added. The resulting mixture was again heated to 75° C., and then reaction was carried out under stirring for one hour. After the reaction was complete, the reaction mixture was cooled to room temperature, and thus precipitated crystalline product was collected by filtration. Subsequently, the crystalline product was placed in 30 mL of aqueous sodium hydroxide (1 mol/L), and the aqueous mixture was stirred for 30 minutes at room temperature. The crystalline product was collected by filtration, washed with 30 mL of water, and dried under reduced pressure, to give 1.91 g (isolated yield: 73%, purity 97% in terms of area percentage determined by high performance liquid chromatography) of 6-iodo-4-anilinoquinazoline as a yellowish crystalline product.

Workup

  1. customIn a 20 mL-volume glass vessel equipped with a stirrer
  2. temperatureThe resulting mixture was heated to 75° C.
  3. customreaction
  4. temperatureSubsequently, the mixture was cooled to room temperature
  5. temperatureThe resulting mixture was again heated to 75° C.
  6. customreaction
  7. stirringunder stirring for one hour
  8. temperaturethe reaction mixture was cooled to room temperature
  9. filtrationthus precipitated crystalline product was collected by filtration
  10. stirringthe aqueous mixture was stirred for 30 minutes at room temperature
  11. filtrationThe crystalline product was collected by filtration
  12. washwashed with 30 mL of water
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-b462fdfacf4b45c3ae0cbecb9f8be619
Source dataset
uspto-grants-2012_11
Patent number
US08318932B2

Reaction notes

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