1,8-Diazabicyclo(5.4.0)undec-7-ene → 2,2,7-trifluoro-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 2176400Notes

Reaction equation

HRID 2176400 reaction equation
Br[C:2]([F:15])([F:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[OH:13])=[O:4].N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[F:14][C:2]1([F:15])[O:13][C:7]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=2[NH:5][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 668361432-bromo-2,2-difluoro-N-(4-fluoro-2-hydroxyphenyl)acetamide

Product 1

HCID 574754482,2,7-trifluoro-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 105.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To 2-bromo-2,2-difluoro-N-(4-fluoro-2-hydroxyphenyl)acetamide (33 g, 116 mmol) in dry Toluene was added 1,8-Diazabicyclo[5.4.0]undec-7-en (DBU, 17.51 ml, 116 mmol). The resulting mixture was stirred overnight at 80° C. The reaction was quenched in saturated aqueous NH4Cl solution and extracted with ethyl acetate. The combined extracts were washed with brine, dried with Na2SO4 and concentrated to afford 24.94 g of the title compound.

Workup

  1. customThe reaction was quenched in saturated aqueous NH4Cl solution
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-03d79ba032b440b38d99e921164f3715
Source dataset
uspto-grants-2015_06
Patent number
US09066519B2

Reaction notes

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