(E)-N-(2-Chloro-6-methylphenyl)-3-etho...

To a cold stirring solution of 2-chloro-6-methylaniline (59.5 g 0.42 mol) and pyridine (68 ml, 0.63 mol) in THF (600 mL) was added 3-ethoxyacryloyl chloride (84.7 g, 0.63 mol) slowly keeping the temp at 0-5°C. The mixture was then warmed and stirred for 2 h. at 20°C. Hydrochloric acid (1N, 115 mL) was added at 0-10°C. The mixture was diluted with water (310 mL) and the resulting solution was concentrated under vacuum to a thick slurry. The slurry was diluted with toluene (275 mL) and stirred for 15 min. at 20-22°C then 1 h. at 0°C. The solid was collected by vacuum filtration, washed with water (2 x 75 mL) and dried to give 74.1 g (73.6 percent yield) of (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide). lH NMR (400 Hz, DMSO-d6) 8 1. 26 (t, 3H, J= 7 Hz), 2.15 (s, 3H), 3.94 (q, 2H, J= 7 Hz), 5.58 (d, 1H, J=12.4 Hz), 7.10-7. 27 (m, 2H, J=7.5 Hz), 7.27-7. 37 (d, 1H, J=7.5 Hz), 7.45 (d, 1H, J=12.4 Hz), 9. 28 (s, 1H) ; l3c NMR (100MHz, CDC13) b : 14. 57, 18.96, 67.17, 97.99, 126. 80, 127. 44, 129. 07, 131.32, 132.89, 138. 25, 161. 09, 165. 36.Ethyl vinyl ether compound of formula-5 (500 gm) was slowly added to oxalyl chloride compound of formula-4 (670 ml) at 10-15°C. Raised the temperature of the reaction mixture to 25-30°C and stirred for 12 hours at the same temperature. Heated the reaction mixture to 120- 125°C and stirred for 90 minutes at the same temperature. Cooled the reaction mixture to 30-35 °C and (E)-3-ethoxyacryloyl chloride compound of formula-7 was collected by fractional distillation. Added tetrahydrofuran (1160 ml) to the obtained compound of formula-7 and cooled the reaction mixture to 10-15°C. Slowly added a solution of 2-methyl-6-chloroaniline compound of formula-9 (290 gm), pyridine (248ml) & tetrahydrofuran (1160 ml) to the reaction mixture at same temperature. Raised the temperature of the reaction mixture to 25-30°C and stirred the reaction mixture for 4 hours at the same temperature. Cooled the reaction mixture to 5-10°C and acidified the reaction mixture using aqueous HC1 solution. Water and ethyl acetate were added to the reaction mixture and stirred for 10 minutes. Separated the both aqueous & organic layers and extracted the aqueous layer with ethyl acetate. Washed the total organic layer with aqueous sodium bicarbonate solution followed by with water. Distilled off the solvent completely from the organic layer under reduced pressure. Ethyl acetate was added to the obtained compound at 25-30°C and cooled the reaction mixture to 0-5°C. Stirred the reaction mixture for 2 hours at the same temperature. Filtered the precipitated solid, washed with chilled ethyl acetate and dried the material to get the title compound.

Molecular Weight:239.70
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:239.0713064
Monoisotopic Mass:239.0713064
Topological Polar Surface Area:38.3
Heavy Atom Count:16
Complexity:255
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes