Chloride → 2H-1,2-Benzoxazin-3(4H)-one

HRID 1883077Notes

Reaction equation

HRID 1883077 reaction equation
C(Cl)Cl.[C:4]([OH:15])(=O)[C:5]1[CH:13]=[CH:12][C:8](C(O)=O)=[CH:7][CH:6]=1.C([N:18](CC)CC)C.[Cl-].[CH3:24][OH:25]>CN(C=O)C>[O:25]1[C:24]2[CH:13]=[CH:12][CH:8]=[CH:7][C:6]=2[CH2:5][C:4](=[O:15])[NH:18]1

Participants

7

Reactant 5

HCID 312ChlorideHCID 887MethanolHCID 6344DichloromethaneHCID 7489Terephthalic AcidHCID 8471Triethylamine

Product 1

HCID 199374482H-1,2-Benzoxazin-3(4H)-oneYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Into 50 mL methylene chloride was dissolved 0.682 g (2 mmol) of the above intermediate terephthalic acid, followed by 5 drops DMF and 3.88 mL (48 mmol) triethylamine. The mixture was cooled in an ice bath, and 0.42 mL (4.8 mmol) oxayl chloride was added in one portion. After 30 min 10 mL MeOH was added and ice bath was removed. After stirring an additional 30 min, the mixture was shaken between EtOAc (100 mL) and cold dilute HCl (100 mL). The organic layer was washed with satd NaHCO3 (100 mL), dried (MgSO4), and evaporated. Crystalline desired benzoxazinone (456 g, 66%) was obtained from a concentrated methylene chloride-hexane solution.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customice bath was removed
  3. stirringthe mixture was shaken between EtOAc (100 mL) and cold dilute HCl (100 mL)
  4. washThe organic layer was washed with satd NaHCO3 (100 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-6cd11bea0efc4658a3ad585acbe23ad0
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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