Pyridine → 2,6-Dimethyl-4-(nonafluoro-2-butyl)phenyl 3-[(2,2,2-trichloroethoxy)carbonylamino]benzamide

HRID 1527625Notes

Reaction equation

HRID 1527625 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([F:21])([C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH3:22])[C:3]=1N.[N:23]1C=CC=CC=1.O1CCCC1.[Cl:34][C:35]([Cl:51])([Cl:50])[CH2:36][O:37][C:38]([NH:40][C:41]1[CH:42]=[C:43]([CH:47]=[CH:48][CH:49]=1)[C:44](Cl)=[O:45])=[O:39]>O.C(OCC)(=O)C>[CH3:22][C:5]1[CH:6]=[C:7]([C:9]([F:21])([C:14]([F:19])([F:20])[C:15]([F:16])([F:17])[F:18])[C:10]([F:11])([F:12])[F:13])[CH:8]=[C:2]([CH3:1])[C:3]=1[C:42]1[C:41]([NH:40][C:38]([O:37][CH2:36][C:35]([Cl:51])([Cl:50])[Cl:34])=[O:39])=[CH:49][CH:48]=[CH:47][C:43]=1[C:44]([NH2:23])=[O:45]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 231237403-[(2,2,2-Trichloroethoxy)carbonylamino]benzoyl chlorideHCID 866700812,6-Dimethyl-4-(nonafluoro-2-butyl)aniline

Product 1

HCID 866700802,6-Dimethyl-4-(nonafluoro-2-butyl)phenyl 3-[(2,2,2-trichloroethoxy)carbonylamino]benzamideYield 71.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

First, to a solution prepared by adding 0.34 g of 2,6-dimethyl-4-(nonafluoro-2-butyl)aniline and 0.09 g of pyridine to 5 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was added 0.33 g of 3-[(2,2,2-trichloroethoxy)carbonylamino]benzoyl chloride produced in Example 9-2. After reaction for 5 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.45 g (yield 71%) of the title compound as a solid.

Workup

  1. customFirst, to a solution prepared
  2. customAfter reaction for 5 hours
  3. customThen, an organic layer was separated
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe filtrate was collected
  7. distillationthe solvent of the filtrate was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-853b85b2f6494717b0e04d88ce691dfc
Source dataset
uspto-grants-2015_07
Patent number
US09089133B2

Reaction notes

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