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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Sodium thiocyanate can reduce pro-inflammatory cytokine IL-6 levels, increase anti-inflammatory cytokine IL-10 levels, and significantly decrease ROS formation, playing an important role in anti-inflammatory research.
Synonyms: Thiocyanate sodium; Sodium rhodanide; Sodium sulfocyanate
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CAS No. : | 540-72-7 |
Formula : | CNNaS |
M.W : | 81.07 |
SMILES Code : | [S-]C#N.[Na+] |
Synonyms : |
Thiocyanate sodium; Sodium rhodanide; Sodium sulfocyanate
|
MDL No. : | MFCD00011123 |
InChI Key : | VGTPCRGMBIAPIM-UHFFFAOYSA-M |
Pubchem ID : | 516871 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302+H312+H332-H318-H412 |
Precautionary Statements: | P261-P264-P270-P271-P273-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338+P310-P501 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With bromine In methanol at -10 - -5℃; for 2 h; | Synthesis of 2-aminobenzothiazole-6-carbolic Acid(2)NaSCN (65 g, 0.8 mol) was added to a suspension of commercially available 4-amino-benzoic acid (1, 100 g, 0.73 mol) in MeOH followed by the addition of Br2 (38 ml, 0.73 mol) in portions. The above solution was allowed to cool to -10° C. and stirred for 2 h while keeping the inner temperature below -5° C. The precipitate was then filtered and suspended in 350 ml of 1 M HCl. The suspension was heated to reflux for 30 min. After immediate filtration, 150 ml concd HCl was added to the hot filtrate to give 70 g (yield 42percent) of 2-amino-benzothiazole-6-carboxylic acid (2) (as a white solid), which was dried and used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With β-cyclodextrin-polyurethane polymercoated Fe3O4 magnetic nanoparticle; In water; at 90.0℃; for 0.583333h; | General procedure: To a mixture of the benzyl halide (1.0 mmol) and MY (Y:N3, SCN, OAc, CN) (2 mmol) in water (5 ml), -CDPU-MNPs (0.1 g) was added. The suspension was magnetically stirred under reflux conditions for the time shown in Table 1. After complete consumption of starting material as judged by TLC (using n-hexane-ethylacetate as eluent), the catalyst was concentrated on the sidewall of the reaction vessel using an external magnet, the aqueous phase was separated by decantation and extracted with diethyl ether (2× 10 mL). The extracted was dried with calcium chloride (CaCl2) and evaporated in vacuo to give corresponding product. The residual catalyst in the reaction vessel was washed and dried and then subjected to the next run directly. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Sodium thiocyanate (527 mg, 6.50 mmol) was dissolved in 20 mL of methanol and placed at -20° C., followed by addition of cyclopropylcarbamidine hydrochloride (603 mg, 5 mmol) and triethylamine (0.8 mL, 5.74 mmol). After stirring for 45 minutes, triethylamine (0.7 mL, 5.02 mmol) and 8percent sodium hypochlorite solution (4.2 mL, 5 mmol) were added dropwise to the reaction mixture. After reacting for 2 hours at -20° C., the reaction mixture was warmed up to room temperature. After reacting for 12 hours, the reaction mixture was concentrated under reduced pressure, followed by addition of 35 mL of H2O and extracted with ethyl acetate (30 mLx3). The organic phases were combined, washed with saturated sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title product 3-cyclopropyl-1,2,4-thiadiazol-5-amine 49a (243 mg, white solid), which was used directly in the next step without further purification. MS m/z (ESI): 142.2 [M+1] | ||
243 mg | Step 1 3-Cyclopropyl-1,2,4-thiadiazol-5-amine Sodium thiocyanate (527 mg, 6.50 mmol) was dissolved in 20 mL of methanol and placed in -20°C, followed by addition of cyclopropylcarbamidine hydrochloride (603 mg, 5 mmol) and triethylamine (0.8 mL, 5.74 mmol). After stirring for 45 minutes, triethylamine (0.7 mL, 5.02 mmol) and 8percent sodium hypochlorite solution(4.2 mL, 5 mmol) were dropwise added into the reaction mixture. After reacting for 2 hours at -20°C, the reaction mixture was warmed up to room temperature. After reacting for 12 hours, the reaction mixture was concentrated under reduced pressure, followed by addition of 35 mL of H2O and extracted with ethyl acetate (30 mL*3). The organic phase was combined, washed with saturated sodium chloride solution (50 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title product 3-cyclopropyl-1,2,4-thiadiazol-5-amine 49a (243 mg, white solid), which was used directly in the next step without further purification. MS m/z (ESI): 142.2 [M+1] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With bromine; acetic acid; at 20℃; for 16h; | 10697] Sodium thiocyanate (1.6 g, 19.8 mmol) was dissolved in acetic acid (20 mE), and 2-bromo-3-methoxyani- line (1 g, 4.95 mmol) dissolved in acetic acid (20 mE) was added dropwise thereto. Afier dropwise addition, bromine (281 pL, 5.45 mmol) dissolved in acetic acid (10 mE) was added dropwise thereto, and the solution was stirred at room temperature. After 16 hours, the solvent was distilled oil under reduced pressure and saturated sodium hydrogen carbonate aqueous solution was added to the residue. The precipitated solids were separated by filtration and the obtained crystals were washed with chloroform (20 mE) and methanol (20 mE) to obtain a title compound (brown crystal, 756 mg, yield of 59%).j0698] ?H NMR (DMSO-d5, 400 MHz): oe=3.87 (s, 3H), 6.84 (d, 1H, J=8 Hz), 7.61 (d, 1H, J=8 Hz), 7.87 (br s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | To a solution of 4-bromo-2-(trifluoromethoxy) aniline (5.00 g, 19.53 mmol) in acetic acid (60 mL) was added NaSCN (6.33 g,78.12 mmol) batchwise at room temperature. The mixture was stirred for 30 min then a solution of Br2 (6.24 g, 39.0 mmol) in acetic acid (10 mL). The resulting mixture was stirred for 8 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was suspended in water. The pH value of the mixture was adjusted to 9 with solid Na2C03. The solids were collected by filtration and washed with water, dried under vacuum. This resulted in 5.70 g (93%) of the title compound as an orange solid (crude product). LC-MS (ESI, m/z): [M+H]+ = 315. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.6% | In methanol; acetonitrile; at 80℃; for 48h;Sealed tube; | 0.5 mmol of N-methyl-benzimidazole-2-aldehyde (a, 0.082 g, also simply referred to as ligand L in this application) was added to a 25 mL capacity polytetrafluoroethylene reactor,10 mL of a mixed solvent consisting of acetonitrile and methanol (V acetonitrile: V methanol = 1: 1),After completely dissolved, continue to add 0.5mmolThorium nitrate hexahydrate(0.228g),After dissolving, add 0.25 mmol of sodium thiocyanate (0.021 g), and finally until it is completely dissolved,Add 0.5 mmol of 1,2-cyclohexanediamine (b, 61 μL) under stirring.Continue to stir for 3 minutes. After sealing, put it in an oven at 80 C for 48 hours, and take it out.Slowly cool down (about 12h to room temperature), white long crystals precipitate,The crystals were collected and dried.Yield 57.6% (based on osmium nitrate hexahydrate). |
Tags: Sodium thiocyanate | Thiocyanate sodium | 540-72-7
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