Trifluoroacetic acid → HCID 17778835, compound
Reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:8][C:7]=1[OH:17])=[O:4].C(=O)([O-])[O-].[K+].[K+].CC#N.O.FC(F)(F)C(O)=O>CN(C)C=O.C(OCC)(=O)C>[F:14][C:13]([F:16])([F:15])[O:12][C:10]1[CH:9]=[CH:8][C:7]2[O:17][CH2:2][C:3](=[O:4])[NH:5][C:6]=2[CH:11]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
2-bromo-N-{2-hydroxy-5-[(trifluoromethyl)oxy]phenyl}acetamide (4.23 g, 13.5 mmol), was dissolved in 140 mL of anhydrous dimethylformamide under argon. Potassium carbonate was added and suspended in the solution at room temperature. The mixture was warmed to 85° C. and was refluxed for one hour. HPLC (Eclipse XDB-C18, 4.6×250 mm, 5 micron, 1-99% CH3CN/H2O with 0.1% trifluoroacetic acid) indicated that all of the starting material (Rt=6.5 min) was consumed and a new single peak formed (Rt=6.2 min). The mixture was allowed to cool to room temperature before it was diluted with 600 mL of ethyl acetate and washed with water (2×150 mL) and brine (2×150 mL). The organic phase was dried over Na2SO4, filtered and concentrated to give 6-[(trifluoromethyl)oxy]-2H-1,4-benzoxazin-3(4H)-one (2.86 g, 12.3 mmol, 91%) as a brown amorphous solid. MS (ES) m/e 233 [M+H]+.
Workup
- customsuspended in the solution at room temperature
- temperaturewas refluxed for one hour
- customwas consumed
- customa new single peak formed (Rt=6.2 min)
- temperatureto cool to room temperature before it
- washwashed with water (2×150 mL) and brine (2×150 mL)
- dry with materialThe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-769edbcc1cc14756ad58836687b459b5
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432258B2
Reaction notes
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