1,2,3-Benzothiadiazole

The raw material o-aminothiophenol (0.3mmol, 1 equiv) and tert-butyl nitrite (0.45mmoia.5equiv) was added to the reaction vessel at room temperature (25 ° C), and then added to the reaction solvent water 2 mL), The reaction was stirred at 25 ° C for 3min, after the reaction, ethyl acetate (10mL) was added to dilute the reaction solution, the diluted solution was transferred to a separatory funnel, extracted with saturated brine, The aqueous phase and the organic phase were separated, and the aqueous phase was extracted with ethyl acetate 2 to 4 times. All the organic phases were combined and then the combined organic phases were dried over anhydrous sodium sulfate (5 g), filtered after 5 min, The filter cake was washed with ethyl acetate (5 mL × 3 times) and then concentrated under reduced pressure. The concentrate was finally separated by column chromatography (3: 1 by volume petroleum ether and ethyl acetate) and the eluate was collected Remove the solvent, a white liquid, yield 96percent.Step A: 1 , 2, 3-benzothiadiazoleTo a mixture of 2-aminobenzenethiol (1.00 g, 7.99 mmol) in water (8 mL) was added aqueous 12 N hydrochloric acid (2 mL, 20 mmol) slowly at rt. Sodium nitrite (827 mg, 12.0 mmol) was then added slowly at rt. THF (4 mL) was added for solubility, and the reaction was stirred at rt for 30 min. The solution was neutralized with saturated aqueous potassium carbonate, and the material was extracted with DCM and saturated aqueous sodium bicarbonate. The organic layer was purified via column chromatography (1 percent EtOAc:heptane) to afford 850 mg (78percent) of the title compound as an orange liquid.

Molecular Weight:136.18
XLogP3:1.9
Hydrogen Bond Acceptor Count:3
Exact Mass:136.00951931
Monoisotopic Mass:136.00951931
Topological Polar Surface Area:54
Heavy Atom Count:9
Complexity:107
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes