Phosphorus oxychloride → 7-(Benzyloxy)-4-chloroquinazoline

HRID 1723720Notes

Reaction equation

HRID 1723720 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:22])=O>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:22])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1357631107-(Benzyloxy)-3,4-dihydroquinazolin-4-one

Product 1

HCID 220309237-(Benzyloxy)-4-chloroquinazolineYield 90%

Procedure

A solution of the product from Step 2 (2.82 g, 11.2 mmol) in phosphorous oxychloride (20 mL) was heated at 100° C. for 16 hours. The reaction was concentrated and azeotroped once with dichlromethane. The residue was dissolved in EtOAc and washed with saturated sodium bicarbonate solution then saturated sodium chloride solution. The organic layer was dried over sodium sulfate and concentrated to provide 7-(benzyloxy)-4-chloroquinazoline (2.72 g, 90%) as a yellow solid. MS 271.2 (ES+).

Workup

  1. concentrationThe reaction was concentrated
  2. customazeotroped once with dichlromethane
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5093888ac35f48c4898f86072bd94d1d
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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