Thionyl Chloride → 4-Chloro-2-(4-chlorophenyl)-6,7-dimethoxyquinazoline

HRID 2408997Notes

Reaction equation

HRID 2408997 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:17][C:16](=O)[C:15]3[C:10](=[CH:11][C:12]([O:21][CH3:22])=[C:13]([O:19][CH3:20])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>CN(C=O)C>[Cl:25][C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:21][CH3:22])=[C:13]([O:19][CH3:20])[CH:14]=2)[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1358250262-(4-Chlorophenyl)-4-hydroxy-6,7-dimethoxyquinazoline

Product 1

HCID 229973614-Chloro-2-(4-chlorophenyl)-6,7-dimethoxyquinazolineYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-6,7-dimethoxyquinazolin-4(3H)-one (200 mg), thionyl chloride (10 mL) and DMF (0.3 mL) was refluxed for 2 h. Solvents were removed under vacuum. The mixture was poured into ice cold water and stirred for 10 min. The solution was basified with ammonia and stirred for 5 min. The solution was extracted with chloroform (3×100 mL) and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the product as an yellow color solid (180 mg, 86%), mp 204-206° C. 1H NMR (400 MHz, DMSO-d6): δ 8.47 (2H, d, J=8.4 Hz), 7.66 (2H, d, J=8.4 Hz), 7.52 (1H, s), 7.44 (1H, s), 4.08 (3H, s), 4.05 (3H, s).

Workup

  1. temperaturewas refluxed for 2 h
  2. customSolvents were removed under vacuum
  3. additionThe mixture was poured into ice cold water
  4. stirringstirred for 5 min
  5. extractionThe solution was extracted with chloroform (3×100 mL)
  6. washthe combined chloroform layer was washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationThe solution was filtered
  9. customevaporated the solvent

Sources & evidence

ORD record
ord-997d3e8c387748eea02be5306407e5d4
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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