Thionyl Chloride → HCID 22030960, compound

HRID 1791697Notes

Reaction equation

HRID 1791697 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][O: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][O: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 1357422856-Methoxy-7-[2-(2-methoxyethoxy)ethoxy]quinazolin-4(1H)-one

Product 1

HCID 22030960HCID 22030960, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)-3,4-dihydroquinazolin-4-one (930 mg, 3.16 mmol) in thionyl chloride (15 ml) and DMF (150 μl) was heated at 60° C. for 1.5 hours. The mixture was allowed to cool and the volatiles were removed by evaporation and by azeotroping with toluene. The residue was dissolved in methylene chloride and 5% aqueous sodium hydrogen carbonate solution was added until the aqueous layer was at pH8. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by flash chromatography eluting with ethyl acetate to give 4-chloro-6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)quinazoline (863 mg, 87%).

Workup

  1. temperatureto cool
  2. customthe volatiles were removed by evaporation
  3. customby azeotroping with toluene
  4. dissolutionThe residue was dissolved in methylene chloride
  5. addition5% aqueous sodium hydrogen carbonate solution was added until the aqueous layer
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed by evaporation
  10. customThe residue was purified by flash chromatography
  11. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-30ee7078ab034fc7a1499a0f7c2a6156
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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