Thionyl Chloride → 4-Chloro-7-(4-pyridylmethoxy)quinazoline hydrochloride

HRID 279544Notes

Reaction equation

HRID 279544 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]3)=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.S(Cl)([Cl:22])=O>CN(C=O)C>[ClH:22].[Cl:22][C:13]1[C:12]2[C:17](=[CH:18][C:9]([O:8][CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[CH:10][CH:11]=2)[N:16]=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1356711817-(4-Pyridylmethoxy)-3,4-dihydroquinazolin-4-one

Product 1

HCID 226250794-Chloro-7-(4-pyridylmethoxy)quinazoline hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
60 °C

Procedure

A mixture of 7-(4-pyridylmethoxy)-3,4-dihydroquinazolin-4-one (320 mg, 1.26 mmol), DMF (1 drop) and thionyl chloride (10 ml) was heated at 60° C. for 1 hour. The volatiles were removed by evaporation, the residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-chloro-7-(4-pyridylmethoxy)quinazoline hydrochloride (435 mg, 98%).

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue was triturated with ether
  3. filtrationcollected by filtration
  4. washwashed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f0f1fe6fe73343df9a762aaf62dec0f1
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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