Toluene → 6-Iodo-4-methoxyquinazoline

HRID 1881674Notes

Reaction equation

HRID 1881674 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:12].P(Cl)(Cl)(Cl)=O.[C:18]1(C)C=CC=CC=1.C(N(CC)CC)C>CO>[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[O:12][CH3:18]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1354016666-Iodoquinazolin-4-one

Product 1

HCID 196057826-Iodo-4-methoxyquinazoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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, 1.24 g (8.09 mmol) of phosphorus oxychloride, and 10 mL of toluene in a nitrogen atmosphere. While the mixture was stirred at room temperature, 0.82 g (8.09 mmol) of triethylamine was slowly added. The resulting mixture was heated to 75° C., and the reaction was carried out for 2 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and 100 mL of methanol was added. The mixture was stirred for 15 minutes at the same temperature, to give 6-iodo-4-methoxyquinazoline. Analysis of the reaction mixture by high performance liquid chromatography indicated that 2.11 g (reaction yield: 99%) of 6-iodo-4-chloroquinazoline was produced.

Workup

  1. customIn a 20 mL-volume glass vessel equipped with a stirrer
  2. temperatureThe resulting mixture was heated to 75° C.
  3. temperaturethe reaction mixture was cooled to room temperature
  4. stirringThe mixture was stirred for 15 minutes at the same temperature

Sources & evidence

ORD record
ord-4f51f9d99fa44cb68dfb09a78d381627
Source dataset
uspto-grants-2012_11
Patent number
US08318932B2

Reaction notes

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