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

HRID 1597217Notes

Reaction equation

HRID 1597217 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(Cl)Cl>[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

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

Product 1

HCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazolineYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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. washwashed with sodium hydrogen carbonate until the aqueous layer
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-82c5b7054800490295b7e7f0151e4519
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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