Thionyl Chloride → 3-(4-Chloroquinazolin-2-yl)phenyl acetate

HRID 1808392Notes

Reaction equation

HRID 1808392 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[NH:20][C:19](=O)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:6]=1)(=[O:3])[CH3:2].S(Cl)([Cl:24])=O>CN(C=O)C>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[N:20]=[C:19]([Cl:24])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1357964653-(4-Oxo-3,4-dihydroquinazolin-2-yl)phenyl acetate

Product 1

HCID 593619303-(4-Chloroquinazolin-2-yl)phenyl acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-(4-oxo-3,4-dihydroquinazolin-2-yl)phenyl acetate was added thionyl chloride (100 mL) and DMF (2 mL) and the reaction was heated to reflux for 4 h. The flask was allowed to cool to RT and then concentrated in vacuo. The crude product was azeotroped with toluene (2×50 mL), taken up in CH2Cl2 (300 mL) and washed with saturated NaHCO3 (3×50 mL), water (1×50 mL) and brine (1×50 mL), dried with MgSO4 and concentrated in vacuo to give 3-(4-chloroquinazolin-2-yl)phenyl acetate. (9.77 g, mmol, 100%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 4 h
  3. concentrationconcentrated in vacuo
  4. customThe crude product was azeotroped with toluene (2×50 mL)
  5. washwashed with saturated NaHCO3 (3×50 mL), water (1×50 mL) and brine (1×50 mL)
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cbb8b4d2e271475dbf960fa9963f5f58
Source dataset
uspto-grants-2013_01
Patent number
US08357693B2

Reaction notes

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