Phosphorus oxychloride → 4-Chloro-6,7-dimethoxy-2-methylquinazoline

HRID 2408988Notes

Reaction equation

HRID 2408988 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([CH3:15])[NH:7][C:6]2=O.P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[C:8]([CH3:15])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354275036,7-Dimethoxy-2-methylquinazolin-4-ol

Product 1

HCID 104901504-Chloro-6,7-dimethoxy-2-methylquinazolineYield 92%

Procedure

A mixture of 6,7-dimethoxy-2-methylquinazolin-4(3H)-one (1.0 mg) and phosphorous oxychloride (20 mL) was refluxed for 3 h. The reaction mixture was attained to rt and poured into ice cold water and stirred for 10 min. The solution was extracted with chloroform (3×100 mL) and the combined CHCl3 layer was washed water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the product as a yellow color solid (1.0 g, 92%), mp 182-184° C. 1H NMR (400 MHz, CDCl3): δ 7.36 (1H, s), 7.30 (1H, s), 4.06 (6H, s), 2.81 (3H, s); LC-MS (positive ion mode): m/z 239, 241 (M+H)+.

Workup

  1. temperaturewas refluxed for 3 h
  2. customwas attained to rt
  3. additionpoured into ice cold water
  4. extractionThe solution was extracted with chloroform (3×100 mL)
  5. washthe combined CHCl3 layer was washed water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered
  8. customevaporated the solvent

Sources & evidence

ORD record
ord-7c2c79afe1b24e61bdf8e903313b691d
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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