Phosphorus oxychloride → 4-Chloro-6-nitroquinazoline

HRID 2199342Notes

Reaction equation

HRID 2199342 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][NH:8][C:7]2=O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:17])=O>CCCCCC>[Cl:17][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1353985026-Nitro-3,4-dihydroquinazolin-4-one

Product 1

HCID 113562574-Chloro-6-nitroquinazolineYield 87.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
160 °C

Procedure

6-Nitro-3H-quinazolin-4-one 4a (18.88 g, 99.40 mmol) was dissolved in phosphoricchloride (31.03 g, 149 mmol). The mixture was warmed up to 160° C., and stirred for 3 hours. The reaction mixture was added to 250 mL of n-hexane while hot, stirred and a lot of the solid was precipitated from the solution, filtered, the filter cake was washed with n-hexane, dried under vacuum to obtain the title compound 4-chloro-6-nitro-quinazoline 4b (18.14 g, yield 87.2%) as a yellow solid.

Workup

  1. stirringstirred
  2. customa lot of the solid was precipitated from the solution
  3. filtrationfiltered
  4. washthe filter cake was washed with n-hexane
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7a1ef8d02e2246fab9cff820bf5136d3
Source dataset
uspto-grants-2016_06
Patent number
US09358227B2

Reaction notes

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