Phosphorus oxychloride → 6-Bromo-4-chloro-7-methyl-8-nitroquinazoline

HRID 1042256Notes

Reaction equation

HRID 1042256 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[CH3:17])[N:13]=[CH:12][NH:11][C:10]2=O>>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[CH3:17])[N:13]=[CH:12][N:11]=[C:10]2[Cl:3]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1358945796-bromo-7-methyl-8-nitroquinazolin-4(3H)-one

Product 1

HCID 589422476-Bromo-4-chloro-7-methyl-8-nitroquinazolineYield 70%

Conditions

Temperature
130 °C

Procedure

A mixture of phosphorous oxychloride (5 mL) and 6-bromo-7-methyl-8-nitroquinazolin-4(3H)-one (800 mg, 2.82 mmol) was refluxed at 130° C. for 4 h. On cooling, POCl3 was removed under reduced pressure. The resulting crude product residue was diluted with ice-water and extracted out of the aqueous layer with DCM (3×20 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to give 6-bromo-4-chloro-7-methyl-8-nitroquinazoline (595 mg, 70% yield) as an amorphous light yellow solid. MS (ESI, pos. ion) m/z: 302 [M+H]+

Workup

  1. temperatureOn cooling
  2. customPOCl3 was removed under reduced pressure
  3. additionThe resulting crude product residue was diluted with ice-water
  4. extractionextracted out of the aqueous layer with DCM (3×20 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-05be6f5597524e3db60ffdce9649be4f
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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