Phosphorus oxychloride → HCID 86692243, compound

HRID 1469751Notes

Reaction equation

HRID 1469751 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=O)[C:9]2[C:4](=[C:5]([N+:13]([O-:15])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:18]>C1(C)C=CC=CC=1>[Cl:18][C:10]1[C:9]2[C:4](=[C:5]([N+:13]([O-:15])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[N:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136098554HCID 136098554, compound

Product 1

HCID 86692243HCID 86692243, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-methyl-8-nitroquinazolin-4(3H)-one (250 mg, 1.22 mmol) in toluene (1 mL) was added POCl3 (374 mg, 2.44 mmol) and the reaction mixture was heated at reflux for 10 h. Then the reaction mixture was concentrated and triturated with Et2O. The precipitate obtained was filtered and dried to afford 150 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.60-8.58 (d, J=7.8 Hz, 1H), 8.52-8.49 (d, J=9.0 Hz, 1H), 7.95-7.89 (t, J=7.8 Hz, 1H), 2.75 (s, 3H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 10 h
  3. concentrationThen the reaction mixture was concentrated
  4. customtriturated with Et2O
  5. customThe precipitate obtained
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-2f7b9b572e244591a9687741b076bf58
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

Loading…