Ethyl Acetate → HCID 44995557, compound

Temperature

0 °C

Ethyl oxalyl chloride (7.8 g, 6.8 mL, 57 mmol) was added to a mixture of 3,4-dimethoxyaniline (4.4 g, 29 mmol) and K2CO3 (14 g, 140 mmol) in EtOAc (44 mL) and water (12 mL) at 0° C. After stirring at 0° C. for 10 min, water (18 mL) was added; whereupon the mixture was transferred to a separatory funnel and extracted with EtOAc (2×40 mL). The combined EtOAc were filtered through Na2SO4 and evaporated to about 30 mL. After addition of 2,2-dimethoxyethylamine (3.8 g, 3.9 mL, 36 mmol), the reaction was stirred at ambient temperature overnight. The resultant white solid was filtered and then washed with hexane to afford N1-(2,2-dimethoxyethyl)-N2-(3,4-dimethoxyphenyl)oxalamide as a light purple-grey solid (6.3 g, 71% yield). HPLC 33% 2.47 min and 63% at 2.79 min. LC MS 1.37 min (M+1=281 and 335). H-NMR (CDCl3) 9.15 (broad s, 1H), 7.76 (broad s, 1H), 7.41 (d, J=2.4 Hz, 1H), 7.06 (dd, J=2.4, 8.7 Hz, 1H), 6.85 (d, J=8.7 Hz, 1H), 4.45 (t, J=5.5 Hz, 1H), 3.90 (s, 3H), 3.88 (s, 3H), 3.52 (t, J=5.5 Hz, 2H), 3.42 (s, 6H).

1. customwhereupon the mixture was transferred to a separatory funnel
2. extractionextracted with EtOAc (2×40 mL)
3. filtrationThe combined EtOAc were filtered through Na2SO4
4. customevaporated to about 30 mL
5. stirringthe reaction was stirred at ambient temperature overnight
6. filtrationThe resultant white solid was filtered
7. washwashed with hexane

ORD record

ord-4352d497d8244c0da1b0154fa53174e0

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08012984B2