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

HRID 1022393Notes

Reaction equation

HRID 1022393 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. II-11) 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 then added, thereby adjusting the pH to 9. Then, precipitated crystals were collected by filtration. The collected product was 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 then added
  3. customThen, precipitated crystals
  4. filtrationwere collected by filtration
  5. customThe collected product was recrystallized from ethanol

Sources & evidence

ORD record
ord-0b7cba995d9c403a817999f31bde628a
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

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