4-(Trifluoromethyl)aniline → 1,1-Dimethylethyl N-[4-(trifluoromethyl)phenyl]carbamate

HRID 42038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 42038
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[C:12]([O:16][C:17](=O)[O:18]C(C)(C)C)([CH3:15])([CH3:14])[CH3:13].[OH-].[Na+]>C1COCC1>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:17](=[O:18])[O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 99644-(Trifluoromethyl)anilineHCID 14798Sodium Hydroxide2×HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester2×

Produkt 1

HCID 112307451,1-Dimethylethyl N-[4-(trifluoromethyl)phenyl]carbamateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 4-trifluoromethylaniline (40 mmol, 5 ml), di-tert-butylcarbonate (40 mmol, 8.7 g), 1N solution of aqueous NaOH (20 ml) in THF (20 ml) was stirred at room temperature for 12 hours. di-tert-butylcarbonate (20 mmol, 4.2 g), 1N solution of aqueous NaOH (20 ml) were added and the mixture was stirred at room temperature for 24 hours. The solvent was evaporated and EtOAc was added. The solution was washed with 2N HCl aqueous solution and brine and then evaporated. The crude mixture was purified by chromatography over SiO2 eluting with hexane/EtOAc mixtures and affording 9.3 g (yield 90%) of the expected product.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. customThe solvent was evaporated
  3. additionEtOAc was added
  4. washThe solution was washed with 2N HCl aqueous solution and brine
  5. customevaporated
  6. customThe crude mixture was purified by chromatography over SiO2 eluting with hexane/EtOAc mixtures

Quellen und Nachweise

ORD-Eintrag
ord-61ae9a9734c54acfbbb6042ab631831c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536165B2

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