Phosphorus oxychloride → 2,8-Dichloro-4-phenylquinazoline

HRID 1022411Notes

Reaction equation

HRID 1022411 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=O)[N:8]=[C:7]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P(Cl)(Cl)([Cl:21])=O.C(=O)(O)[O-].[Na+]>>[Cl:21][C:9]1[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178517435HCID 178517435, compound

Product 1

HCID 866395192,8-Dichloro-4-phenylquinazolineYield 80.5%

Conditions

Temperature
95 °C

Procedure

To 1.24 g of 8-chloro-4-phenyl-2(1H)-quinazolinone (compound No. IV-4) was added 6.65 g of phosphorus oxychloride, followed by stirring at 95° C. for 1 hour. The resulting reaction solution was poured into 200 ml of ice water and sodium bicarbonate was added thereto, thereby adjusting the pH 9. Then, precipitated crystals were collected by filtration and recrystallized from ethanol to obtain 1.07 g of the titled compound. Mp.154.4.° C. 1H NMR (CDCl3): 7.52-7.65 (4H, m), 7.76-7.80 (2H, m), 8.02-8.08 (2H, m).

Workup

  1. customThe resulting reaction solution
  2. additionwas added
  3. customThen, precipitated crystals
  4. filtrationwere collected by filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-89153e47fdb7459f98df4be36c7234f8
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

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