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

HRID 634752Notes

Reaction equation

HRID 634752 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][NH:16][CH2:17][CH2:18][O:19][CH3:20])[N:9]=[CH:8][NH:7][C:6]2=O.S(Cl)([Cl:24])=O>CN(C=O)C>[Cl:24][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][O:19][CH3:20])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 135549385HCID 135549385, compound

Product 1

HCID 212603294-Chloro-6-methoxy-7-(2-(2-methoxyethylamino)ethoxy)quinazolineYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-methoxy-7-(2-(2-methoxyethylamino)ethoxy)-3,4-dihydroquinazolin-4-one (300 mg, 1 mmol), thionyl chloride (5 ml) and DMF (0.1 ml) was heated at reflux for 45 minutes. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The resulting gum was partitioned between aqueous sodium hydrogen carbonate solution and methylene chloride. The organic layer was separated and the aqueous layer extracted with methylene chloride (4×40 ml). The combined extracts were passed through phase separating paper and the solvent removed by evaporation to give 4-chloro-6-methoxy-7-(2-(2-methoxyethylamino)ethoxy)quinazoline (120 mg, 38%) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 45 minutes
  3. customExcess thionyl chloride was removed by evaporation
  4. customthe residue azeotroped with toluene
  5. customThe resulting gum was partitioned between aqueous sodium hydrogen carbonate solution and methylene chloride
  6. customThe organic layer was separated
  7. extractionthe aqueous layer extracted with methylene chloride (4×40 ml)
  8. customseparating paper
  9. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-159778b95fc342c09e341025b31cc266
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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