Thionyl Chloride → 4-Chloro-7-(3-morpholinopropoxy)quinazoline hydrochloride

HRID 1596282Notes

Reaction equation

HRID 1596282 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.C1(C)C=CC=CC=1>[ClH:24].[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

5

Reactant 2

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

Product 1

HCID 217015574-Chloro-7-(3-morpholinopropoxy)quinazoline hydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one (200 mg, 0.69 mmol) in thionyl chloride (5 ml) and DMF (0.1 ml) was heated at reflux for 1 hour. The solution was diluted with toluene and the volatiles removed by evaporation. The residue was dissolved in methylene chloride and ether was added. The resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-chloro-7-(3-morpholinopropoxy)quinazoline hydrochloride (238 mg, 100%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customthe volatiles removed by evaporation
  4. dissolutionThe residue was dissolved in methylene chloride
  5. additionether was added
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-ad3c4ae9d13745b0a6ed3acde770c3c2
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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