Phosphorus oxychloride → 4-Chloro-8-iodo-7-methylquinazoline

HRID 2092281Notes

Reaction equation

HRID 2092281 reaction equation
P(Cl)(Cl)([Cl:3])=O.[I:6][C:7]1[C:8]([CH3:18])=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][NH:13][C:12]2=O>>[Cl:3][C:12]1[C:11]2[C:16](=[C:7]([I:6])[C:8]([CH3:18])=[CH:9][CH:10]=2)[N:15]=[CH:14][N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1357422708-Iodo-7-methylquinazolin-4(3H)-one

Product 1

HCID 584664844-Chloro-8-iodo-7-methylquinazolineYield 92.1%

Procedure

Phosphorous oxychloride (19.5 mL, 210 mmol) and 8-iodo-7-methylquinazolin-4(3H)-one (2.00 g, 6.99 mmol) were added to a round bottomed flask. The reaction mixture was heated at reflux for 2 h. Upon cooling, excess POCl3 was removed under reduced pressure and the remaining crude product dissolved in DCM (100 mL) and washed with ice-cold water (300 mL) to remove excess acid. The crude residue dissolved in DCM was then dried over anhydrous sodium sulfate and concentrated in vacuo to give 4-chloro-8-iodo-7-methylquinazoline (1.96 g, 92%) as an amorphous brown solid. MS (M+H)+ 305.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureUpon cooling
  4. customexcess POCl3 was removed under reduced pressure
  5. dissolutionthe remaining crude product dissolved in DCM (100 mL)
  6. washwashed with ice-cold water (300 mL)
  7. customto remove excess acid
  8. dissolutionThe crude residue dissolved in DCM
  9. dry with materialwas then dried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e49a33527614665983a269f9f8a6479
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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