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5919-29-9

ETHYL 2-ACETAMIDO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE synthesis

8synthesis methods
-

Yield:5919-29-9 100%

Reaction Conditions:

in acetic acid at 85; for 24 h;

Steps:

10.4 (4) Synthesis of Ethyl 2-Acetylamino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-ca rboxylate

A mixture of ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxyl ate (25 g, 111 mmol), acetic acid (150 mL), and acetic anhydride (19 mL, 200 mmol) was stirred at 85°C for 24 hours. To this reaction solution, 100 mL of water was added, and the precipitates were collected by filtration to obtain ethyl 2-acetylamino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-ca rboxylate (30 g, quant.) as a white solid: TLC Rf=0.38 (n-hexane/ethyl acetate=3/1); 1H NMR (500 MHz, CDCl3) δ 1.38 (t, J=7.0 Hz, 3H), 1.76-1.81 (m, 4H), 2.25 (s, 3H), 2.63 (t, J=4.5 Hz, 2H), 2.76 (t, J=4.5 Hz, 2H), 4.32 (q, J=7.0 Hz, 2H), 11.26 (br s, 1H); 13C NMR (126 MHz, CDCl3) δ 14.5, 23.1, 23.2, 23.9, 24.6, 26.6, 60.7, 111.5, 126.9, 130.9, 147.8, 166.9, 167.1.

References:

EP2813226,2014,A1 Location in patent:Paragraph 0157; 0158