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

HRID 1184334
Notes
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Reaction equation

HRID 1184334 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-5bfdaaafa0e048ada95ec9938d5a9d91
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08669208B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes