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

HRID 1386269Notes

Reaction equation

HRID 1386269 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 excess thionyl chloride was removed by evaporation and by azeotroping with toluene to give 7-benzyloxy4-chloro-6-methoxyquinazoline hydrochloride (3.45 g), which was subjected to an aqueous work-up with sodium hydroxide solution to give 7-benzyloxy-4-chloro-6-methoxyquinazoline.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customThe excess thionyl chloride was removed by evaporation
  4. customby azeotroping with toluene

Sources & evidence

ORD record
ord-05b3231fd0b34abc9cff72e50469a863
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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