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

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

7synthesis methods

Product Name:3-AMINO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER
CAS Number:34761-09-6
Molecular formula:C11H11NO2S
Molecular Weight:221.28

394-47-8

623-51-8

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

34761-09-6

The general procedure for the synthesis of ethyl 3-aminobenzo[B]thiophene-2-acetate from 2-fluorobenzonitrile and ethyl mercaptoacetate is as follows: Method 1: Synthesis of 4-aminobenzothiophene from 3,4-dipyrimidine 1A. Ethyl 3-amino-carboxylate 2-fluorobenzonitrile (8.25 mmol), diisopropylethylamine (8.25 mmol), and ethyl 2-mercaptoacetate (8.25 mmol) were dissolved in anhydrous N,N-dimethylformamide (5 mL) and stirred for 30 min at room temperature. Potassium carbonate (8.25 mmol) was then added and the reaction mixture was heated to 80 °C and maintained for 20 hours. Upon completion of the reaction, the reaction was quenched by the addition of ice water, the precipitate was collected by filtration and washed with water to afford the target product carboxylate as a white solid in 92% yield. LCMS retention time 7.43 min, [M + H]+ 222; 1H-NMR (CDCl3) 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).

394-47-8 Synthesis

394-47-8
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$5.00/5g

623-51-8
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$7.00/25g

34761-09-6
65 suppliers
$20.00/250mg

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

7716-66-7 Synthesis