| Identification | Back Directory | [Name]
(E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide | [CAS]
863127-76-8 | [Synonyms]
SKL777
(E)-N-(2-CHLORO-6-METHYLPHENYL)-3-ETHOXYACRYLAMIDE
(Z)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide
(E) - N - (2-chloro-6-methylphenyl) -5-thiazolamide
(2E)-N-(2-Chloro-6-methylphenyl)-3-ethoxy-acrylamide
(E)-N-(2-chloro-6-methyl-phenyl)-3-ethoxyl acrylamide
(E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyprop-2-enamide
(2E)-N-(2-Chloro-6-methylphenyl)-3-ethoxy-2-propenamide
(2E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyprop-2-enamide
2-PropenaMide,N-(2-chloro-6-Methylphenyl)-3-ethoxy-, (2E)-
(E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide 863127-76-8 | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C12H14ClNO2 | [MDL Number]
MFCD13185963 | [MOL File]
863127-76-8.mol | [Molecular Weight]
239.7 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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. | [Application]
(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 |
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