ChemicalBook CAS DataBase List 2,7-Dichlorobenzothiazole

2,7-Dichlorobenzothiazole synthesis

5synthesis methods

Product Name:2,7-Dichlorobenzothiazole
CAS Number:2942-23-6
Molecular formula:C7H3Cl2NS
Molecular Weight:204.08

2(3H)-Benzothiazolethione,7-chloro-(9CI)

1849-73-6
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$9.00/100mg

2942-23-6
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$25.00/100mg

Yield: 94%

Reaction Conditions:

Stage #1:2-mercapto-7-chlorobenzothiazole with sulfuryl dichloride at 20 - 25; for 0.25 h;Inert atmosphere;
Stage #2: with water at 20 - 25; for 3 h;Inert atmosphere;

Steps:

Chlorination Using Sulfuryl Chloride/Water; General Procedure
General procedure: A mixture of the 2-mercaptobenzo[d]thiazole (>1 g, 1 equiv) and sul-furyl chloride (10 equiv) was stirred at 20-25 °C for 15 min. Next, H 2 O(2 equiv) was added and the mixture was stirred at 20-25 °C for anadditional 3 h. A sample was taken, quenched with MeCN/H 2 O (2:1)and analyzed by HPLC. After completion of the reaction, the mixturewas diluted with MeCN (5 volumes) and slowly quenched with H 2 O(20 volumes). The product precipitated from the aqueous solution.The solid was collected and washed with H 2 O. Drying under vacuumafforded the pure product. In the case of the liquid product 2-chloro-benzo[d]thiazole (13), the reaction mixture was extracted withEtOAc. The organic layer was then dried and concentrated to affordthe product as an oil.

References:

Wimmer, Laurin;Parmentier, Michael;Riss, Bernard;Kapferer, Tobias;Ye, Chao;Li, Lei;Kim, Hongyong;Li, Jialiang [Synthesis,2018,vol. 50,# 10,p. 2027 - 2032]