Thionyl Chloride → 4-Chloro-6-methoxy-7-(2-methylthioethoxy)quinazoline

HRID 634697Notes

Reaction equation

HRID 634697 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][S:16][CH3:17])[N:9]=[CH:8][NH:7][C:6]2=O.S(Cl)([Cl:21])=O>CN(C=O)C>[Cl:21][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][S:16][CH3:17])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 135549387HCID 135549387, compound

Product 1

HCID 212603184-Chloro-6-methoxy-7-(2-methylthioethoxy)quinazolineYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 6-methoxy-7-(2-methylthioethoxy)-3,4-dihydroquinazolin-4-one (1.07 g, 4.0 mmol), thionyl chloride (20 ml) and DMF (4 drops) was heated at reflux for 2 hours and then allowed to cool. The excess thionyl chloride was removed by evaporation and the residue was azeotroped with toluene. The solid residue was partitioned between aqueous sodium hydrogen carbonate and methylene chloride, the organic phase was separated and washed with brine. The organic phase was passed through phase separating paper, and the solvent removed by evaporation to give 4-chloro-6-methoxy-7-(2-methylthioethoxy)quinazoline (810 mg, 71%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. customThe excess thionyl chloride was removed by evaporation
  5. customthe residue was azeotroped with toluene
  6. customThe solid residue was partitioned between aqueous sodium hydrogen carbonate and methylene chloride
  7. customthe organic phase was separated
  8. washwashed with brine
  9. customseparating paper
  10. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-8b1004e3364f4826945ed33eff86f52a
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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