ChemicalBook CAS DataBase List 4-CYANOTHIOPHENOL

4-CYANOTHIOPHENOL synthesis

10synthesis methods

Product Name:4-CYANOTHIOPHENOL
CAS Number:36801-01-1
Molecular formula:C7H5NS
Molecular Weight:135.19

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Yield:36801-01-1 100%

Reaction Conditions:

Stage #1:4-bromobenzenecarbonitrile with caesium carbonate;copper(II) sulfate in dimethyl sulfoxide for 0.166667 h;Inert atmosphere;
Stage #2: with ethane-1,2-dithiol in dimethyl sulfoxide at 100; for 20 h;Inert atmosphere;

Steps:

16.1 Step 1:- Preparation of 4-mercaptobenzonitrile
To the stirred solution of 4-bromobenzonitrile (5 g, 27.5 mmol) in dimethyl sulfoxide (100 mL), copper (II) sulfate (0.2 g, 1.4 mmol) and cesium carbonate (45 g, 137 mmol) were added. The reaction mixture was degassed with nitrogen for 10 min, 1 ,2-ethanedithiol (4.6 mL, 55 mmol) was added and the reaction mixture was heated to 100 °C for 20 h. Upon completion of the reaction, the reaction mixture was heated to 25 °C and quenched with 10% hydrochloric acid solution till the pH 1-2 was attained. Ethyl acetate (40 mL) was added to aqueous layer and biphasic mixture was filtered through celite bed to remove insoluble inorganic junk. Aqueous layer was extracted thrice with ethyl acetate (180 mL). The combined ethyl acetate layer was washed with ice cold water (90 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain 4-mercaptobenzonitrile (3.7 g, 27 mmol, 100 % yield).

References:

PI INDUSTRIES LTD.;BHUJADE, Paras Raybhan;NAIK, Maruti N;PAWAR, Rajesh;TRIVEDI, Pooja;DENGALE, Rohit Arvind;KULKARNI, Shantanu Ganesh;TEMBHARE, Nitin Ramesh;AUTKAR, Santosh Shridhar;GARG, Ruchi;VENKATESHA, Hagalavadi M;KLAUSENER, Alexander G.M. WO2020/70610, 2020, A1 Location in patent:Page/Page column 113

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