Acetic Acid → 6-Bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

HRID 2406199Notes

Reaction equation

HRID 2406199 reaction equation
C[O-].[Na+].[Br:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[S:15])[N:9](C(OCC)=O)[C:8]2=[O:21].C(O)(=O)C>CO.C1COCC1>[Br:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[S:15])[NH:9][C:8]2=[O:21]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 86652648HCID 86652648, compound

Product 1

HCID 8408566-Bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-oneYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium methoxide (0.5 M, 36.1 mmol) in methanol (72 mL) was added to a solution of 3a (10.8 g, 32.8 mmol) in 150 mL of dry THF and the mixture was heated at reflux for 90 min. The mixture was allowed to reach room temperature and quenched by addition of acetic acid (2.1 mL, 36.1 mmol). The mixture was concentrated under reduced pressure and 200 mL of ethyl alcohol and 100 mL of water was added and the mixture was heated at reflux for 30 min. The slurry was cooled to rt. and filtrated to give 4 white solid (8.43 g, 100%). mp: 350° C. (decomp.),

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 90 min
  3. customto reach room temperature
  4. concentrationThe mixture was concentrated under reduced pressure and 200 mL of ethyl alcohol and 100 mL of water
  5. additionwas added
  6. temperaturethe mixture was heated
  7. temperatureat reflux for 30 min
  8. filtrationand filtrated

Sources & evidence

ORD record
ord-a738b6ec754f4677acfbedfda58ab9dc
Source dataset
uspto-grants-2014_08
Patent number
US08809355B2

Reaction notes

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