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

HRID 22772

Reaction equation

HRID 22772 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][NH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C(=O)NC=1.S(Cl)([Cl:34])=O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:34])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178486491HCID 178486491, compound

Product 1

HCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After repetition of the reaction so described, a mixture of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-3,4-dihydroquinazolin-4-one (20.3 g), thionyl chloride (440 ml) and DMF (1.75 ml) was heated to reflux for 4 hours. The thionyl chloride was evaporated under vacuum and the residue was azeotroped with toluene three times to give 7-benzyloxy-4-chloro-6-methoxyquinazoline.

Workup

  1. customAfter repetition of the reaction
  2. temperaturewas heated
  3. temperatureto reflux for 4 hours
  4. customThe thionyl chloride was evaporated under vacuum
  5. customthe residue was azeotroped with toluene three times

Sources & evidence

ORD record
ord-e5fecba0e55c40a8881f1cf893e0b073
Source dataset
uspto-grants-2005_02
Patent number
US06849625B2

Linked notes

Loading…