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

HRID 1357712Notes

Reaction equation

HRID 1357712 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>[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 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (20.3 g), thionyl chloride (440 ml) and DMF (1.75 ml) was stirred and heated to reflux for 4 hours. The thionyl chloride was evaporated and the residue was azeotroped with toluene three times to give crude 7-benzyloxy-4-chloro-6-methoxyquinazoline.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. customThe thionyl chloride was evaporated
  4. customthe residue was azeotroped with toluene three times

Sources & evidence

ORD record
ord-fee23423dd36440b97558004d86ad7df
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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