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4-Nitrobenzoyl chloride → N-[2,6-Dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-nitro-benzamide

HRID 587845
Notes
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Reaction equation

HRID 587845 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:13][C:14]1[CH:20]=[C:19]([C:21]([F:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])[CH:18]=[C:17]([Cl:31])[C:15]=1[NH2:16]>N1C=CC=CC=1.O>[Cl:13][C:14]1[CH:20]=[C:19]([C:21]([F:30])([C:26]([F:27])([F:28])[F:29])[C:22]([F:25])([F:24])[F:23])[CH:18]=[C:17]([Cl:31])[C:15]=1[NH:16][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 100194962,6-Dichloro-4-(perfluoropropan-2-yl)aniline

Product 1

HCID 86666630N-[2,6-Dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-nitro-benzamideYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

4-Nitrobenzoyl chloride (4.55 g) was dissolved in a pyridine (30 ml) solution of 2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)aniline (2.7 g). The solution was refluxed under heating for 3 hours. After cooling to room temperature, the solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined and dried over magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off under reduced pressure. The residue was dissolved in tetrahydrofuran (30 ml), and an aqueous solution (5 ml) containing sodium hydroxide (2.0 g) was added, and then stirred at room temperature for 4 hours. The reaction solution was extracted twice with ethyl acetate. The organic phases were combined, washed with 1 N hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The drying agent (i.e., anhydrous magnesium sulfate) was removed by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to obtain N-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-nitrobenzamide (3.27 g, yield 83.4%).

Workup

  1. temperatureThe solution was refluxed
  2. temperatureunder heating for 3 hours
  3. extractionextracted twice with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. dissolutionThe residue was dissolved in tetrahydrofuran (30 ml)
  8. additionan aqueous solution (5 ml) containing sodium hydroxide (2.0 g)
  9. additionwas added
  10. extractionThe reaction solution was extracted twice with ethyl acetate
  11. washwashed with 1 N hydrochloric acid and water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe drying agent (i.e., anhydrous magnesium sulfate) was removed by filtration
  14. distillationthe solvent was distilled off under reduced pressure
  15. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-afa2eaff3ed44196a0b21be2c5b44259
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09227923B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes