2-(Trifluoromethyl)aniline → HCID 117853269, compound

HRID 530187Notes

Reaction equation

HRID 530187 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.[F:19][C:20]1[C:28]([N:29]([CH3:38])[C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23].[OH-].[Na+]>O1CCCC1>[F:19][C:20]1[C:28]([N:29]([CH3:38])[C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=1[C:2]([F:10])([F:11])[F:1])=[O:23]

Participants

6

Reactant 4

HCID 69222-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 58298670HCID 58298670, compound

Product 1

HCID 117853269HCID 117853269, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

26.8 g (166.3 mmol) of 2-(trifluoromethyl)aniline, 37.0 g (365.9 mmol) of triethylamine, and 100.9 g (365.9 mmol) of 2-fluoro-3-(N-methylbenzamido)benzoyl chloride were added to tetrahydrofuran (400 mL), and the mixture was stirred at 50° C. for 3 hours. The reaction liquid was filtered through a filter, and an aqueous solution (125 mL) containing 14.6 g (365.9 mmol) of sodium hydroxide was added to the filtrate, followed by stirring at 50° C. for 30 minutes. After the solvent was distilled off under reduced pressure, the obtained residue was extracted with ethyl acetate, and washed with aqueous potassium carbonate solution and saturated saline solution, sequentially. The organic layer was dried over magnesium sulfate. Then, magnesium sulfate was filtered off, and the solvent was distilled off under reduced pressure. The obtained solid was washed with n-hexane and isopropyl ether, followed by drying, to obtain 63.2 g (yield 91%) of the title compound as a white solid.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through a filter
  3. additionwas added to the filtrate
  4. stirringby stirring at 50° C. for 30 minutes
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. extractionthe obtained residue was extracted with ethyl acetate
  7. washwashed with aqueous potassium carbonate solution and saturated saline solution
  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. washThe obtained solid was washed with n-hexane and isopropyl ether
  12. customby drying

Sources & evidence

ORD record
ord-2033ecb01ecf47c691cf170374462116
Source dataset
uspto-grants-2016_05
Patent number
US09353046B2

Reaction notes

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