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Dimethylformamide → HCID 86686558, compound

HRID 1528071
Notes
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Reaction equation

HRID 1528071 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:16])([CH3:15])[C:5](=[O:14])[NH:6]2.FC(F)(F)S(O[CH2:23][C:24]([F:27])([F:26])[F:25])(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:16])([CH3:15])[C:5](=[O:14])[N:6]2[CH2:23][C:24]([F:27])([F:26])[F:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 86686556HCID 86686556, compound

Product 1

HCID 86686558HCID 86686558, compoundYield 1,610.7%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A suspension of 4-fluoro-3,3-dimethyl-5-nitro-1,3-dihydro-2H-indol-2-one (0.10 g), 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.16 g), potassium carbonate (0.12 g) and DMF (2 mL) was stirred at room temperature for 1 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.2 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ffeb99279e724ec1beb8de0a64b01257
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090586B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes