Sodium Hydroxide → 2-Methyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline

HRID 641130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 641130
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:14]=[C:13]([C:15](F)([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:11][C:9]=1[NH2:10].[OH-].[Na+]>O1CCCC1>[CH3:7][C:8]1[CH:14]=[C:13]([CH:15]([C:16]([F:17])([F:18])[F:19])[C:20]([F:23])([F:22])[F:21])[CH:12]=[CH:11][C:9]=1[NH2:10]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 99255434-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)-2-methylanilineHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 129940302-Methyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]anilineAusbeute 221,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 30 ml of tetrahydrofuran (THF) was added 0.5 g (13.2 mmol) of lithium aluminum hydride. While keeping the resulting suspension at a temperature of 0° C., a solution of 13.8 g (20 mmol) of 2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline in 20 ml of THF was dropped into the suspension with stirring over a period of 15 minutes. After completion of the dropping, the resulting mixture was stirred at room temperature for 30 minutes, and then heated under reflux for one hour to make progress a reaction. The reaction mixture was poured into ice water, 20 ml of 1N-aqueous solution of sodium hydroxide was added, and the resulting mixture was stirred. The mixture was extracted with 50 ml of methyl tert-butyl ether, the organic layer was dried on anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by distillation under reduced pressure. Thus, 11.4 g (yield: 89%) of 2-methyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (Compound No. 1-3) was obtained as a fraction having a boiling point of 103° C. (6 mmHg). (1-2) In 10 ml of acetonitrile was dissolved 750 mg (2.0 mmol) of N-(1,1-dimethyl-2-methylthioethyl)-6-iodophthalic acid isoimide, to which were added 515 mg (2.0 mmol) of 2-methyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline and 10 mg of trifluoroacetic acid. The mixture was stirred at room temperature for 2 hours. The deposited crystal was collected by filtration and washed with a small quantity of ether. Thus, 1.0 g of the objective compound was obtained (yield: 79%).

Aufarbeitung

  1. customat a temperature of 0° C.
  2. stirringAfter completion of the dropping, the resulting mixture was stirred at room temperature for 30 minutes
  3. temperatureheated
  4. temperatureunder reflux for one hour
  5. customa reaction
  6. additionwas added
  7. stirringthe resulting mixture was stirred
  8. extractionThe mixture was extracted with 50 ml of methyl tert-butyl ether
  9. dry with materialthe organic layer was dried on anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. distillationthe residue was purified by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b04f711642224267bc7cb2e44b3a59f2
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696129B2

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