Acetic Acid → 2-Chloro-N-(2-ethyl-6-methylphenyl)acetamide

HRID 482210

Reaktionsgleichung

[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH2:6]([C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:9]=1[NH2:10])[CH3:7].C(O)(=O)C.C([O-])(=O)C.[Na+]>O>[Cl:1][CH2:2][C:3]([NH:10][C:9]1[C:11]([CH3:15])=[CH:12][CH:13]=[CH:14][C:8]=1[CH2:6][CH3:7])=[O:4]

Komponenten

Reaktionsbedingungen

Temperatur: 10 °C

Versuchsvorschrift

Chloroacetyl chloride (84.8 g) was added, over 20 minutes, to a solution of 2-ethyl-6-methylaniline (67.5 g), glacial acetic acid (230 ml), sodium acetate (anhydrous 110.5 g) in water (200 ml) at such a rate that the reaction temperature did not exceed 10° C. The resulting suspension was then stirred vigorously for 30 minutes at 10° C. (requiring the addition of further quantities of acetic acid and water to maintain fluidity). The suspension was filtered, the resulting solid was air-dried on the filter and was then recrystallised from ethanol/water to yield the N-chloroacetyl-2-ethyl-6-methylaniline as a colourless solid (58.7 g), m.p. 122°-123° C. This product (10.8 g) was dissolved in toluene and added dropwise to a stirred mixture of N-chloroacetyl-2-ethyl-6-methylaniline (21.2 g), polyethyleneglycol-400 (8.0 g), sodium hydroxide (16.0 g in 15 ml water) and toluene at such a rate to maintain the reaction temperature at 10°-15° C. for 2 hours.

Aufarbeitung

customdid not exceed 10° C
temperatureto maintain fluidity)
filtrationThe suspension was filtered
customthe resulting solid was air-dried on the
filtrationfilter
customwas then recrystallised from ethanol/water

Quellen und Nachweise

ORD-Eintrag: ord-63f82ce41ac94965814233944bcb4ad0
Quelldatensatz: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05795846

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