Phosphorus oxychloride → 4-Chloro-7-ethoxy-6-methoxyquinazoline

HRID 1917634Notes

Reaction equation

HRID 1917634 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=O)[NH:9][CH:10]=[N:11]2)=[CH:6][C:5]=1[O:15][CH3:16])[CH3:2].O=P(Cl)(Cl)[Cl:19]>C1(C)C=CC=CC=1>[Cl:19][C:8]1[C:7]2[C:12](=[CH:13][C:4]([O:3][CH2:1][CH3:2])=[C:5]([O:15][CH3:16])[CH:6]=2)[N:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1355332107-ethoxy-6-methoxyquinazolin-4(3H)-one

Product 1

HCID 117705294-Chloro-7-ethoxy-6-methoxyquinazolineYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7-ethoxy-6-methoxyquinazolin-4(3H)-one (1.20 g, 5.45 mmol) and POCl3 (3 mL), in toluene (10 mL) was heated at 125° C. for 5 hours. It was concentrated under reduced pressure to dryness. To it was added CH2Cl2 and it was washed with saturated NaHCO3. The organic layer was dried over MgSO4 and concentrated to give 4-chloro-7-ethoxy-6-methoxyquinazoline as solid (1.254 g, 96%). 1H NMR (300 MHz, CDCl3) δ 8.91 (s, 1H), 7.52 (s, 1H), 7.42 (s, 1H), 4.34 (q, 2H), 4.08 (s, 3H), 1.59 (t, 3H).

Workup

  1. concentrationIt was concentrated under reduced pressure to dryness
  2. additionTo it was added CH2Cl2 and it
  3. washwas washed with saturated NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1f5c405e738a4921af3eaba2101ece8b
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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