Thionyl Chloride → 4-Chloro-7-(3-(morpholin-4-yl)propoxy)quinazoline

HRID 1386322Notes

Reaction equation

HRID 1386322 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:20]=[C:19]3[C:14]([C:15](=O)[NH:16][CH:17]=[N:18]3)=[CH:13][CH:12]=2)[CH2:3][CH2:2]1.S(Cl)([Cl:24])=O>CN(C=O)C>[Cl:24][C:15]1[C:14]2[C:19](=[CH:20][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:12][CH:13]=2)[N:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1357987527-(3-Morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Product 1

HCID 216992974-Chloro-7-(3-(morpholin-4-yl)propoxy)quinazolineYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one (500 mg, 1.7 mmol), thionyl chloride (10 ml) and DMF (0.1 ml) was heated at reflux for 2 hours. The volatiles were removed by evaporation and the residue azeotroped with toluene. The crude product was partitioned between methylene chloride (50 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml) and the mixture stirred for 10 minutes. The organic phase was separated and the aqueous phase extracted with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed by evaporation to give 4-chloro-7-(3-morpholinopropoxy)quinazoline (425 mg, 80%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe volatiles were removed by evaporation
  4. customthe residue azeotroped with toluene
  5. customThe crude product was partitioned between methylene chloride (50 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml)
  6. customThe organic phase was separated
  7. extractionthe aqueous phase extracted with methylene chloride
  8. dry with materialThe combined extracts were dried (MgSO4)
  9. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-ba680be453f24c109c4a381d8fd980c5
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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