(E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide Chemical Properties

Boiling point:

386.5±42.0 °C(Predicted)

Density 

1.197

storage temp. 

Sealed in dry,Room Temperature

pka

11.57±0.70(Predicted)

InChI

InChI=1S/C12H14ClNO2/c1-3-16-8-7-11(15)14-12-9(2)5-4-6-10(12)13/h4-8H,3H2,1-2H3,(H,14,15)/b8-7+

InChIKey

DBYFNZJHXGNAGW-BQYQJAHWSA-N

SMILES

C(NC1=C(C)C=CC=C1Cl)(=O)/C=C/OCC

Safety Information

HS Code 

2924297099

(E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide Usage And Synthesis

Uses

(2E)-N-(2-Chloro-6-methylphenyl)-3-ethoxy-2-propenamide is a reagent used for the preparation of potent and selective anti-tumor drug Dasatinib.

Synthesis

3-Ethoxyacryloyl chloride (84.7 g, 0.63 mol) was slowly added dropwise to a tetrahydrofuran (THF, 600 mL) solution of 2-chloro-6-methylaniline (59.5 g, 0.42 mol) and pyridine (68 ml, 0.63 mol) cooled to 0-5°C with stirring, maintaining the reaction temperature at 0-5°C. After completion of the drop, the reaction mixture was gradually warmed to 20°C and stirring was continued for 2 hours. Subsequently, the reaction solution was cooled to 0-10°C and acidified by slowly adding 1N hydrochloric acid (115 mL). The reaction mixture was diluted with water (310 mL) and concentrated under reduced pressure to a thick slurry. The thick slurry was diluted with toluene (275 mL) and stirred at 20-22°C for 15 minutes, then continued stirring at 0°C for 1 hour. The precipitated solid was collected by vacuum filtration, washed with water (2 x 75 mL) and dried to give (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide 74.1 g in 73.6% yield. The product was characterized by 1H NMR (400 MHz, DMSO-d6) and 13C NMR (100 MHz, CDCl3) with the following data: 1H NMR δ 1.26 (t, 3H, J=7Hz), 2.15 (s, 3H), 3.94 (q, 2H, J=7Hz), 5.58 (d, 1H, J=12.4Hz), 7.10- 7.27 (m, 2H), 7.27-7.37 (d, 1H, J=7.5Hz), 7.45 (d, 1H, J=12.4Hz), 9.28 (s, 1H); 13C NMR δ 14.57, 18.96, 67.17, 97.99, 126.80, 127.44, 129.07, 131.32. 132.89, 138.25, 161.09, 165.36.

References

[1] Archiv der Pharmazie, 2011, vol. 344, # 7, p. 451 - 458
[2] Patent: WO2005/77945, 2005, A2. Location in patent: Page/Page column 50-51
[3] Arkivoc, 2010, vol. 2010, # 6, p. 32 - 38
[4] Patent: WO2017/2131, 2017, A1. Location in patent: Page/Page column 17; 18

(E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide(863127-76-8)Related Product Information

• ETHYL 2-(TERT-BUTOXYCARBONYLAMINO)THIAZOLE-5-CARBOXYLATE
• 2-N-BOC-AMINO-THIAZOLE-5-CARBOXYLIC ACID
• 2-Chloro-6-methylaniline
• 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
• N-(2-Chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide
• Dasatinib monohydrate
• Dasatinib
• (E)-3-Ethoxyacryloyl chloride
• Acrylamide
• Epichlorohydrin
• N,N'-Methylenebisacrylamide
• N-Methylolacrylamide
• Methacrylamide
• Difluorochloromethane
• Chloroacetic acid
• Ethoxy
• (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide