Sodium Bicarbonate → 1-(2-Amino-5-chlorophenyl)-2,2,2-trifluoroethanone

HRID 377954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377954
O.Cl.[Cl:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH:5]=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.O>[Cl:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11](=[O:16])[C:12]([F:14])([F:15])[F:13])[CH:5]=1

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 441819891-(2-Amino-5-chlorophenyl)-2,2,2-trifluoroethan-1-one--hydrogen chloride--water (1/1/1)

Produkt 1

HCID 109878821-(2-Amino-5-chlorophenyl)-2,2,2-trifluoroethanoneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Chloro-2-trifluoroacetylaniline, hydrochloride hydrate (17.1 g, 62 mmol) was stirred in a mixture of toluene (100 mL) and water (50 mL). The mixture was neutralized to pH 7 with saturated NaHCO3. The organic phase was concentrated in vacuo and the residue recrystallized from heptane to give 12.5 g (91%) of the title compound as yellow needles: mp 98-99° C.; 1H NMR (300 MHz, CDCl3) δ7.70 (t, J=2 Hz, 1H), 7.32 (dd, J=2, 9 Hz, 1H), 6.7 (d, J=9 Hz, 1H), 6.44 (brs, 2H); 13C NMR (75 MHz CDCl3) δ 180.0, 151.6, 136.9, 130.1 , 120.9, 119.0, 116.8, 111.4; 19F NMR (282 MHz, CDCl3) δ-70.3.

Aufarbeitung

  1. concentrationThe organic phase was concentrated in vacuo
  2. customthe residue recrystallized from heptane

Quellen und Nachweise

ORD-Eintrag
ord-9e66e2f6fef9454796a43c0d6ab91582
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028237

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