Thionyl Chloride → 6-Bromo-4-chloro-7-methoxyquinazoline

HRID 240991Notes

Reaction equation

HRID 240991 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[CH:7][NH:6][C:5]2=O.S(Cl)([Cl:17])=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[CH:7][N:6]=[C:5]2[Cl:17]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1357423626-Bromo-7-methoxy-3,4-dihydroquinazolin-4-one

Product 1

HCID 866478096-Bromo-4-chloro-7-methoxyquinazolineYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

6-bromo-7-methoxyquinazolin-4(3H)-one (53 mg, 0.21 mmol) was taken into thionyl chloride (1.5 mL) followed by addition of catalytic DMF. The mixture was heated to 80° C. for 2 h then concentrated. The residue was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with brine then dried over anhydrous sodium sulfate, filtered and concentrated to give 6-bromo-4-chloro-7-methoxyquinazoline (36 mg, 62% yield) as a brown solid. MS (EI) for C9H6BrClN2O: 275 (MH+).

Workup

  1. concentrationthen concentrated
  2. customThe residue was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate
  3. washThe organic phase was washed with brine
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f8d1ecd110c04fd58e84b98c6bfc56b4
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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