Sodium Hydroxide → 2-Fluoro-3-(N-methylbenzamido)-N-(2-methyl-4-(heptafluoroisopropyl)phenyl)benzamide

HRID 530190Notes

Reaction equation

HRID 530190 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:19]([N:20]([CH3:29])[C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=[CH:16][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=[O:7].[F:30][C:31]([F:40])([F:39])[C:32](I)([F:37])[C:33]([F:36])([F:35])[F:34]>CN(C)C=O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[F:3][C:4]1[C:19]([N:20]([CH3:29])[C:21](=[O:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=[CH:16][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:32]([F:37])([C:33]([F:36])([F:35])[F:34])[C:31]([F:40])([F:39])[F:30])=[CH:11][C:10]=1[CH3:15])=[O:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 33978Perfluoroisopropyl iodideHCID 1178532842-fluoro-3-(N-methylbenzamido)-N-(2-methyl-phenyl)benzamide

Product 1

HCID 1178533442-Fluoro-3-(N-methylbenzamido)-N-(2-methyl-4-(heptafluoroisopropyl)phenyl)benzamideYield 30%

Reagents, catalysts & solvents 2

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 6228DimethylformamideSolvent2×

Procedure

0.55 g (14 mmol) of powdery sodium hydroxide and 0.64 g (2.3 mmol) of iron(II) sulfate heptahydrate were stirred in an ice bath, until the color of the mixture changed to black. Immediately after the discoloration, 3 g of N,N-dimethylformamide were added thereto, and then, a solution obtained by dissolving 0.60 g (1.7 mmol) of 2-fluoro-3-(N-methylbenzamido)-N-(2-methyl-phenyl)benzamide and 0.68 (2.3 mmol) of heptafluoroisopropyl iodide in 3 g of N,N-dimethylformamide was added thereto, followed by stirring at room temperature for 3 hours. The obtained reaction liquid was filtered through cerite and the residue was washed with 50 mL of ethyl acetate. Then, 40 g of water were added to the resulting reaction liquid, and after performing extraction, the organic layer was dried over magnesium sulfate. Then, magnesium sulfate was filtered off, and the solvent was distilled off under reduced pressure. Thereafter, the condensed residue was purified by silica gel chromatography, to obtain 0.26 g (yield 30%) of the title compound as a white solid.

Workup

  1. customa solution obtained
  2. additionwas added
  3. customThe obtained reaction liquid
  4. filtrationwas filtered through cerite and the residue
  5. washwas washed with 50 mL of ethyl acetate
  6. additionThen, 40 g of water were added to the resulting reaction liquid
  7. extractionextraction
  8. dry with materialthe organic layer was dried over magnesium sulfate
  9. filtrationThen, magnesium sulfate was filtered off
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThereafter, the condensed residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7c6cf66370de4f1a9bbc39de6bcf22e7
Source dataset
uspto-grants-2016_05
Patent number
US09353046B2

Reaction notes

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