Aniline → Phenylamino-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester

HRID 77026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77026
[CH2:1]([O:3][C:4](=[O:21])[CH:5](OS(C)(=O)=O)[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:2].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>C(#N)C>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 6115Aniline2×HCID 81531DiisopropylethylamineHCID 59401272Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester

Produkt 1

HCID 59401228Phenylamino-(4-trifluoromethyl-phenyl)-acetic acid ethyl esterAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester (I102) (594 mg, 1.82 mmol), aniline (0.25 mL, 2.73 mmol), and DIPEA (0.48 mL, 2.73 mmol) are dissolved in acetonitrile (4 mL). The reaction is heated under microwave irradiation at 100° C. for 1 hour and 30 minutes. Aniline (0.17 mL, 1.820 mmol) is added again and the reaction is heated under microwave irradiation at 100° C. for 3 hours. Acetonitrile is removed under vacuum and the residue is purified by flash chromatography (Petroleum ether/DCM=75/25) to afford intermediate I151 as a yellow oil (195 mg, 60% yield).

Aufarbeitung

  1. temperaturethe reaction is heated under microwave irradiation at 100° C. for 3 hours
  2. customAcetonitrile is removed under vacuum
  3. customthe residue is purified by flash chromatography (Petroleum ether/DCM=75/25)

Quellen und Nachweise

ORD-Eintrag
ord-8545127f95aa4575b0973415b8ec7e40
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835682B2

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