Dimethylformamide → 4-Chloroquinazolin-6-yl acetate

HRID 240565Notes

Reaction equation

HRID 240565 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2O)(=[O:3])[CH3:2].CN(C=O)C.S(Cl)([Cl:23])=O>>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[Cl:23])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178475361HCID 178475361, compound

Product 1

HCID 189676244-Chloroquinazolin-6-yl acetateYield 90%

Conditions

Temperature
90 °C

Procedure

To a solution of 4-hydroxyquinazolin-6-yl acetate (12.0 g, 58.8 mmol) in thionyl chloride (50 mL) was added DMF (0.5 mL). After heating to 90° C. for 3 hours, the reaction mixture was concentrated under reduced pressure and azeotroped with toluene to provide the product (11.8 g, 90%) as off-white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-acb70a8f0bf444479b6502866ef4df74
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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