* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sulfuryl dichloride In (2S)-N-methyl-1-phenylpropan-2-amine hydrate at 0℃; for 1.25 h;
5-Chloro-benzenethiazole-2-thiol, obtained from Aldrich, (2 g, 9.9 mmol) was added slowly to sulfuryl chloride, obtained from Aldrich, (20 mL) and stirred for 1 h followed by heating to 50° C. for 15 minutes. The mixture was cooled, poured slowly over ice water and stirred for 30 minutes. The product precipitated out of solution as a yellow solid and was collected by vacuum filtration and dried under a stream of air followed by high vacuum to give 1.92 g (96percent) of compound 250. 1H NMR (400 MHz, DMSO-d6) δ 8.18 (d, J=8.7 Hz, 1H), 8.1 (d, J=2.0, 1H), 7.59 (dd, J=8.7, 2.1 Hz, 1H).
75%
Stage #1: at 20 - 25℃; for 0.25 h; Inert atmosphere Stage #2: at 20 - 25℃; for 3 h; Inert atmosphere
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.
61%
at 20 - 60℃; for 2 h;
Step 2. 2,5-Dichlorobenzo[d]thiazole. 5-Chloro-2-mercaptobenzothiazole (1 g, 4.96 mmol) was added in portions over 0.5 hour to 10 mL of sulfuryl chloride at r.t. After addition, the reaction mixture was stirred at r.t. for 1 hr, and then heated to 60°C for 0.5 hr. The resulting mixture was cooled to r.t. and added slowly to ice. The mixture was stirred for 0.5 hr and extracted with EtOAc. Combined organic layers were dried over anhydrous Na2S04 and concentrated. The residue was purified by column chromatography to give 2,5-dichlorobenzo[d]thiazole (0.62 g, 61percent yield) as a grey solid. LC-MS: m/z: 204(M+H)+.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
