Phosphorus oxychloride → 2-Chloro-5-methoxy-3-methylquinazolin-4(3H)-one

HRID 598072Notes

Reaction equation

HRID 598072 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:15])[N:6]([CH3:14])[C:7](=O)[NH:8]2.C(N(CC)C(C)C)(C)C.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:7]1[N:6]([CH3:14])[C:5](=[O:15])[C:4]2[C:9](=[CH:10][CH:11]=[CH:12][C:3]=2[O:2][CH3:1])[N:8]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 672670575-methoxy-3-methyl-1H-quinazoline-2,4-dione

Product 1

HCID 672666982-Chloro-5-methoxy-3-methylquinazolin-4(3H)-oneYield 99.6%

Procedure

A mixture of 5-methoxy-3-methyl-1H-quinazoline-2,4-dione (165 mg, 0.800 mmol) and N,N-diisopropylethylamine (0.307 ml, 1.76 mmol) in phosphorus oxychloride (2.2 ml, 24.0 mmol) was refluxed for 18 h with stirring and concentrated to dryness under vacuum. The residue was diluted with water. The aqueous solution was extracted with dichloromethane. The extract was washed with water, dried over magnesium sulfate and concentrated under vacuum to afford 179 mg (99%) of the title compound. The residue was used for the next reaction without further purification.

Workup

  1. temperaturewas refluxed for 18 h
  2. concentrationconcentrated to dryness under vacuum
  3. additionThe residue was diluted with water
  4. extractionThe aqueous solution was extracted with dichloromethane
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f689a00b142e4eb1b1f347283c07613c
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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