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Water → 2-chloro-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-3-nitrobenzamide

HRID 590913
Notes
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Reaction equation

HRID 590913 reaction equation
CN1C(=O)N(C)CC1.[Br:9][C:10]1[CH:16]=[C:15]([C:17]([F:29])([C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])[C:18]([F:21])([F:20])[F:19])[CH:14]=[C:13]([Br:30])[C:11]=1[NH2:12].[Cl:31][C:32]1[C:40]([N+:41]([O-:43])=[O:42])=[CH:39][CH:38]=[CH:37][C:33]=1[C:34](Cl)=[O:35].O>C(OCC)(=O)C>[Cl:31][C:32]1[C:40]([N+:41]([O-:43])=[O:42])=[CH:39][CH:38]=[CH:37][C:33]=1[C:34]([NH:12][C:11]1[C:10]([Br:9])=[CH:16][C:15]([C:17]([F:29])([C:22]([F:27])([F:28])[C:23]([F:24])([F:25])[F:26])[C:18]([F:19])([F:20])[F:21])=[CH:14][C:13]=1[Br:30])=[O:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 126274132-Chloro-3-nitrobenzoyl chlorideHCID 582974122,6-Dibromo-4-(perfluorobutan-2-yl)aniline

Product 1

HCID 866542442-chloro-N-(2,6-dibromo-4-(perfluorobutan-2-yl)phenyl)-3-nitrobenzamideYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To 27 ml of DMI were added 9.90 g (21.1 mmol) of 2,6-dibromo-4-(perfluorobutan-2-yl)aniline and 4.60 g (20.9 mmol) of 2-chloro-3-nitrobenzoyl chloride, followed by stirring at 140° C. for 4 hours. To the reaction solution were added water and ethyl acetate, and the organic phase was extracted, and washed with 1 mol/L of an aqueous sodium hydroxide solution, saturated brine, and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=20:1→10:1→5:1→3:1) to prepare 5.44 g (yield 40%) of a target compound.

Workup

  1. extractionthe organic phase was extracted
  2. washwashed with 1 mol/L of an aqueous sodium hydroxide solution, saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThen, the solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=20:1→10:1→5:1→3:1)

Sources & evidence

ORD record
ord-a3596cb98eb24f9eae17f4bcb146dbc0
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09237745B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes