Benzoyl chloride, 3-nitro- → N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}3-nitrobenzamide

HRID 1696957Notes

Reaction equation

HRID 1696957 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH3:19])[C:3]=1[NH2:4].[N+:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27])([O-:22])=[O:21].C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O.C(OCC)(=O)C.O1CCCC1.N1C=CC=CC=1>[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([OH:18])([C:10]([F:12])([F:13])[F:11])[C:14]([F:15])([F:16])[F:17])[CH:6]=[C:5]([CH3:19])[C:3]=1[NH:4][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][CH:31]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=1

Participants

9

Reactant 4

HCID 8495Benzoyl chloride, 3-nitro-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 12753462-(4-Amino-3,5-dimethylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86616583N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}3-nitrobenzamideYield 98.7%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

At room temperature, 5.0 g of 2,6-dimethyl-4-[1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline, 3.9 g of 3-nitrobenzoyl chloride and 2.1 g of pyridine were introduced to 50 ml of tetrahydrofuran in a reaction vessel, and the resulting mixture was stirred at room temperature. After disappearance of the starting raw material was confirmed by means of TLC, to the reaction solution was added saturated baking soda solution and stirred for a while. Subsequently, ethyl acetate and water were added to the reaction solution for solution separation. Anhydrous magnesium sulfate was added to a separated organic layer, the organic layer was dried and filtered off. The filtrate was evaporated to be dried and the resulting solid was pulverized to obtain 7.5 g of the desired product (Yield: 95%) in the form of powder.

Workup

  1. stirringstirred for a while
  2. customthe organic layer was dried
  3. filtrationfiltered off
  4. customThe filtrate was evaporated
  5. customto be dried

Sources & evidence

ORD record
ord-d056a9d0ebe941dc9d0d69bd5a25b186
Source dataset
uspto-grants-2012_04
Patent number
US08163804B2

Reaction notes

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