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120650-90-0

2-CYANO-3-(DIMETHYLAMINO)-2-BUTENAMIDE synthesis

2synthesis methods
18871-66-4 Synthesis
1,1-Dimethoxy-N,N-dimethylethylamine

18871-66-4
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2-Butenamide, 2-cyano-3-(dimethylamino)-, (2Z)-

120651-05-0
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2-CYANO-3-(DIMETHYLAMINO)-2-BUTENAMIDE

120650-90-0
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Yield:-

Reaction Conditions:

in ethanol; for 2.5 h;Reflux;Overall yield = 57 %; Overall yield = 3.08 g;

Steps:

38 PREPARATION 382-Cyano-3-(dimethylamino)but-2-enamide

1 ,1-Dimethoxy-N,N-dimethylethanamine (5.20 ml, 35.6 mmol) was added dropwise to a suspension of cyanoacetamide (3.00 g, 35.7 mmol) in absolute ethanol (65 ml) and the mixture was stirred and heated to reflux. After 2.5 h, the mixture was cooled and the precipitate was filtered, washed with ethanol and dried to give 3.08 g (20.1 mmol, 57% yield) of the title compound (mixture of cis/trans isomers) as a yellow solid. Purity100%.1H NMR (300 MHz, DMSO-d6) ppm 6.60 (br s, 2H), 3.04 (s, 3H), 2.98 (s, 3H), 2.20 (s, 3H).UPLC/MS (3 mm) retention time 0.46 mm.LRMS: mlz 154 (M+1).

References:

WO2017/60488,2017,A1 Location in patent:Page/Page column 69; 70