N-(4-CHLORO-6-ETHOXYPHENYL)-2,2-DIMETHYLPROPANAMIDE synthesis
- Product Name:N-(4-CHLORO-6-ETHOXYPHENYL)-2,2-DIMETHYLPROPANAMIDE
- CAS Number:922162-66-1
- Molecular formula:C13H18ClNO2
- Molecular Weight:255.74
116278-66-1
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Yield:922162-66-1 95%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 20; for 19 h;
Steps:
4.1.1.42. N-(4-Chloro-2-ethoxyphenyl)-2,2-dimethylpropanamide (10d)
Compound 10j (303 mg, 1.33 mmol) was dissolved in DMF (10 ml). K2CO3 (139 mg, 1.00 mmol) and iodoethane (160 μl, 2.00 mmol) were added to the solution, and the mixture was stirred at room temperature for 19 h. The reaction mixture was concentrated in vacuo, and the residue was dissolved in AcOEt (20 ml), 1 N HClaq (2 ml) and H2O (15 ml). The layers were separated, and the organic layer was washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (n-hexane/AcOEt = 8:1) to give compound 10d (325 mg, 1.27 mmol, 95%) as pale yellow oil. 1H NMR (CDCl3) δ 1.31 (9H, s), 1.47 (3H, t, J = 7.1 Hz), 4.08 (2H, q, J = 7.1 Hz), 6.84 (1H, d, J = 2.2 Hz), 6.92 (1H, dd, J = 8.5, 2.2 Hz), 8.10 (1H, br), 8.33 (1H, d, J = 8.5 Hz). IR (ATR) cm-1 3440, 2974, 1674, 1601, 1514, 1389, 1255, 1124, 1038, 943, 820, 586. MS (ESI) m/z 256 [(M+H)+, Cl35], 258 [(M+H)+, Cl37].
References:
Ichikawa, Masanori;Yokomizo, Aki;Itoh, Masao;Haginoya, Noriyasu;Sugita, Kazuyuki;Usui, Hiroyuki;Terayama, Koji;Kanda, Akira [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 17,p. 5207 - 5224] Location in patent:experimental part
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