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

HRID 227230Notes

Reaction equation

HRID 227230 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>[Cl:24][C:13]1[C:12]2[C:17](=[CH:18][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:10]([O:20][CH3:21])[CH:11]=2)[N:16]=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 7-benzyloxy-6-methoxy-4-quinazolinone (1 g, 3.5 mmol, from Step D), thionyl chloride (5 mL) and DMF (5 drops) was heated at reflux for 4 h. After cooling excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene to afford the intermediate, 4-chloro-6-methoxy-7-benzyloxyquinazoline, as a yellow solid (652 mg, 62%). MS(ES) 301 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. customwas removed by evaporation
  4. customthe residue azeotroped with toluene

Sources & evidence

ORD record
ord-58fc0ca12d7c4a16b3284286a8dc16f0
Source dataset
uspto-grants-2009_07
Patent number
US07560461B2

Reaction notes

Loading…