Thionyl Chloride → 7-(Benzyloxy)-4-chloro-6-methoxyquinazoline hydrochloride

HRID 1597216Notes

Reaction equation

HRID 1597216 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>CN(C=O)C>[ClH:24].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:24])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-one

Product 1

HCID 220308367-(Benzyloxy)-4-chloro-6-methoxyquinazoline hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (2.82 g, 0.01 mol), thionyl chloride (40 ml) and DMF (0.28 ml) was stirred and heated at reflux for 1 hour. The mixture was evaporated and azeotroped with toluene to give 7-benzyloxy-4-chloro-6-methoxyquinazoline hydrochloride (3.35 g). 7-Benzyloxy-4-chloro-6-methoxyquinazoline hydrochloride (3.35 g) was dissolved in methylene chloride (250 ml) and washed with sodium hydrogen carbonate until the aqueous layer was adjusted to pH8. The organic layer was washed with brine, dried (MgSO4) and evaporated to give 7-benzyloxy-4-chloro-6-methoxyquinazoline (2.9 g, 96%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customThe mixture was evaporated
  4. customazeotroped with toluene

Sources & evidence

ORD record
ord-0cc4337bd6de4a0fb85eef1cca193e63
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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