3-Aminobenzoic Acid → 3-[(Trifluoroacetyl)amino]benzoic acid

HRID 1644243

Reaktionsgleichung

Reaktionsgleichung von HRID 1644243
O=C(C1C=CC=CC=1)C[O:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH:7]=1.NC1C=C(C=CC=1)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[F:15][C:14]([F:16])([F:17])[C:13]([NH:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[C:5]([OH:19])=[O:4])=[O:18]

Komponenten

5

Edukt 3

HCID 74193-Aminobenzoic AcidHCID 9845Trifluoroacetic anhydrideHCID 11593542-Oxo-2-phenylethyl 3-[(trifluoroacetyl)amino]benzoate3×

Produkt 1

HCID 2838403-[(Trifluoroacetyl)amino]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A compound having general Formula 4, exemplified by 3-(2,2,2-Trifluoro-acetylamino)-benzoic acid 2-oxo-2-phenyl-ethyl ester (Compound 4; FIG. 1): can be prepared as follows. A solution of 3-aminobenzoic acid (137 mg, 1.0 mmol) in dichloromethane is treated with trifluoroacetic anhydride (420 mg, 2.0 mmol). The reaction mixture is stirred until no further reaction occurs. The reaction mixture is concentrated to give 3-(2,2,2-Trifluoro-acetylamino)-benzoic acid. A solution of 3-(2,2,2-Trifluoro-acetylamino)-benzoic acid (233 mg, 1.0 mmol) and 2-hydroxyacetophenone (136 mg, 1.0 mmol) in dimethylformamide and diisopropylethylamine (260 mg, 2.0 mmol) is treated with HBTU (379 mg, 1.0 mmol). The reaction mixture is stirred until no further reaction occurs. The reaction is poured into ethyl acetate and water. The organic phase is collected, dried and concentrated to give the title compound.

Aufarbeitung

  1. customcan be prepared
  2. concentrationThe reaction mixture is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-304cd3a7fc2741df9afbb97c8fd81e0a
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124612B2

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