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

HRID 634709Notes

Reaction equation

HRID 634709 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][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[N:9]=[CH:8][NH:7][C:6]2=O.S(Cl)([Cl:25])=O>CN(C=O)C>[ClH:25].[Cl:25][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1355424376-Methoxy-7-(2-piperidinoethoxy)-3,4-dihydroquinazolin-4-one

Product 1

HCID 220308104-Chloro-6-methoxy-7-(2-piperidinoethoxy)quinazoline hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 6-methoxy-7-(2-piperidinoethoxy)-3,4-dihydroquinazolin-4-one (440 mg, 1.45 mmol), thionyl chloride (15 ml) and DMF (3 drops) was heated at reflux for 3 hours then allowed to cool. The excess thionyl chloride was removed by evaporation and the residue was azeotroped with toluene to give a crude 4-chloro-6-methoxy-7-(2-piperidinoethoxy)quinazoline hydrochloride (640 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureto cool
  4. customThe excess thionyl chloride was removed by evaporation
  5. customthe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-1073554ccb1d4c229ed843d382251661
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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