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ChemicalBook CAS DataBase List 3-AMINO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER
34761-09-6

3-AMINO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER synthesis

7synthesis methods
-

Yield:34761-09-6 92%

Reaction Conditions:

Stage #1: 2-fluorobenzonitrile;ethyl 2-sulfanylacetatewith N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide at 20; for 0.5 h;
Stage #2: with potassium carbonate in N,N-dimethyl-formamide at 80; for 20 h;

Steps:

1.1A

Method 1 : 4-Aminobenzothienof3,2-dlpyrimdineSynthesis 1AEthyl 3-amin -carboxylate2-Fluorobenzonitrile (8.25 mmol), diisopropylethylamine (8.25 mmol) and ethyl2-mercaptoacetate (8.25 mmol) in anhydrous Ν,Ν-dimethylformamide (5 mL) was allowed to stir for 30 min at room temperature. Potassium carbonate (8.25 mmol) was added and the solution was heated to 80°C for 20 h. Ice-water was added and the resulting precipitate was filtered off, washing with water to obtain the carboxylate as a white solid (92%).LCMS rt 7.43, M+H 222; 1H-NMR (CDCI3) δ 7.43 (1H, d, J 8.1 Hz), 7.65 (1H, d, J 8.1 Hz), 7.49-7.44 (1H, m), 7.39-7.34 (1H, m), 4.36 (2H, q, J 7.1 Hz), 1.40 (3H, t, J 7.1 Hz).

References:

WO2012/131297,2012,A1 Location in patent:Page/Page column 85

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