ChemicalBook CAS DataBase List 2-Mercaptobenzoxazole

2-Mercaptobenzoxazole synthesis

9synthesis methods

Product Name:2-Mercaptobenzoxazole
CAS Number:2382-96-9
Molecular formula:C7H5NOS
Molecular Weight:151.19

2-Mercaptobenzoxazole has already been described in 1876 by Dunner (Ber. 9, (1876) page 465). 2-Mercaptobenzoxazole and its derivatives are prepared by processes which are based in principle on the reaction between o-aminophenol and alkali metal alkylxanthates. The alkali metal alkylxanthate here can either be employed as such, or it can be produced in the reaction mixture itself from an alkali, a lower alkanol and carbon disulphide.
https://patents.google.com/patent/US4677209A/en

137-26-8
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$10.00/25g

95-55-6 Synthesis

95-55-6
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2382-96-9
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$6.00/5g

Yield:2382-96-9 80%

Reaction Conditions:

Stage #1:2-amino-phenol with potassium carbonate in N,N-dimethyl-formamide for 0.0833333 h;
Stage #2:Thiram in N,N-dimethyl-formamide at 120; for 12 h;Reagent/catalyst;Solvent;Temperature;

Steps:

Typical procedure for the preparation of 2-mercaptobenzoxazoles in the presence of K2CO3 (TP2)
General procedure: 2-Aminophenol (1.0 mmol), K2CO3 (3.0 mmol) was dissolved in DMF (3 mL) in a dried tube, equipped with a magnetic stirring bar and a septum. The mixture was stirred for 5 minutes, and then TMTD (0.6 mmol) was added. The reaction mixture was then heated at 120 °C and checked by TLC until the starting material was finished (around 12 hours). The reaction was cooled down to room temperature, and then quenched with sat. NH4Cl solution and extracted with ethyl acetate, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography to afford the desired product.

References:

Liu, Min;Zeng, Meng-Tian;Xu, Wan;Wu, Li;Dong, Zhi-Bing [Tetrahedron Letters,2017,vol. 58,# 46,p. 4352 - 4356] Location in patent:supporting information

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