4-Fluoro-2-methylaniline → N-Benzyl-2-(4-fluoro-2-methyl-phenylamino)acetamide

HRID 2065753

Reaktionsgleichung

[CH2:1]([NH:8][C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([CH3:21])[CH:15]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([NH:8][C:9](=[O:12])[CH2:10][NH:18][C:17]1[CH:19]=[CH:20][C:14]([F:13])=[CH:15][C:16]=1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of N-benzyl-2-chloro-acetamide (20 g) in DMF (200 mL) were added 4-fluoro-2-methylaniline (13.3 mL) and N,N-diisopropylethylamine (22.2 mL). The reaction mixture was heated to 100° C. over night, cooled to room temperature, and the mixture was diluted with ethyl acetate and washed with water. The combined inorganic phases were extracted with ethyl acetate and the combined organic phases were dried (Na2SO4), filtered and evaporated. The crude product was purified by chromatography (SiO2, n-heptane/ethyl acetate 1:2) to give N-benzyl-2-(4-fluoro-2-methyl-phenylamino)-acetamide (20 g) as grey solid, MS: 273.0 ([M+H]+).

Aufarbeitung

temperaturecooled to room temperature
washwashed with water
extractionThe combined inorganic phases were extracted with ethyl acetate
dry with materialthe combined organic phases were dried (Na2SO4)
filtrationfiltered
customevaporated
customThe crude product was purified by chromatography (SiO2, n-heptane/ethyl acetate 1:2)

Quellen und Nachweise

ORD-Eintrag: ord-56b571d341e943328d87c64f5167373e
Quelldatensatz: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08288541B2

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