Phosphorus oxychloride → 4-CHLORO-5,6,7-TRIMETHOXYQUINAZOLINE

HRID 536069Notes

Reaction equation

HRID 536069 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[C:9]2[C:4]=1[C:5](=O)[N:6]=[CH:7][NH:8]2.O=P(Cl)(Cl)[Cl:20]>CN(C=O)C>[Cl:20][C:5]1[C:4]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[C:12]([O:13][CH3:14])[C:3]=2[O:2][CH3:1])[N:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178486915HCID 178486915, compound

Product 1

HCID 107534804-CHLORO-5,6,7-TRIMETHOXYQUINAZOLINEYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
100 °C

Procedure

5,6,7-tris(methyloxy)-4(1H)-quinazolinone (0.8 g, 3.39 mmol) was treated with POCl3 (10 ml, 107 mmol) and one drop of DMF, and stirred at 100° C. for 1 hour before being concentrated. The residue was treated with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic extracts were dried (sodium sulfate) and concentrated to give 4-chloro-5,6,7-tris(methyloxy)quinazoline (770 mg, 89%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.88 (s, 1 H), 7.37 (s, 1 H), 4.04 (s, 3 H), 3.94 (s, 3 H), 3.91 (s, 3 H). MS (m/z) 255.0 (M+H+).

Workup

  1. concentrationbefore being concentrated
  2. additionThe residue was treated with saturated aqueous NaHCO3
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic extracts were dried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ebde6946b1484551b1f4e0f92eccc36e
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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