4,4´-Diaminodiphenyl ether (Merck)
tert-Butyl acetoacetate (Acros Organics)
DMAP (Merck)

A mixture of 4,4´-diaminodiphenyl ether (1.0 g, 4.99 mmol), tert-butyl acetoacetate (1.63 mL, 9.98 mmol) and DMAP (364 mg, 2.99 mmol) in toluene (20 mL) was refluxed overnight. The reaction mixture was cooled to room temperature, the precipitated product was collected by filtration and washed with cold diethyl ether (3x5 mL) and dried. The title compound was obtained as a cream coloured solid (1.71 g, 93% yield).

Aromatic bisacetoacetamides are useful as intermediates in the production of bisacetoacetanilide azo dyes, pigments and polymeric colorants.
This reaction was carried out by Nilüfer Hamarat in the  final year research project under my supervision.

IR-ATR:  3279, 3254, 3140, 3071, 2920, 1713, 1651, 1611, 1534, 1497, 1221, 1162, 838 cm^-1.
¹H NMR (400 MHz, DMSO-d₆): ppm = 2.21 (s, 6H, CH₃), 3.54 (s, 4H, CH₂), 6.96 (d, 4H, J= 8.86 Hz, CH_Ar), 6.96 (d, 4H, J=8.86 Hz, CH_Ar), 10.08 (s, 2H, NH).
¹³C NMR (100 MHz, DMSO-d₆): ppm = 203.3, 165.26, 153.09, 134.91, 121.24, 119.3, 52.72, 30.62.

Janine Cossy, Annie Thellend, A 4-Dimethylaminopyridine-Catalyzed Aminolysis of β-Ketoesters. Formation of β-Ketoamides, Synthesis, 1989, 753-755.

Jusong Xia, John W. Miley, Aromatic Bis-Acetoacetamide Intermediates, U.S. Patent, 6500935 B2, 2002.