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Type | HazMat fee for 500 gram (Estimated) |
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Structure of 58249-61-9
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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.
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CAS No. : | 58249-61-9 |
Formula : | C8H4N2S |
M.W : | 160.20 |
SMILES Code : | N#CC1=CC=C2N=CSC2=C1 |
MDL No. : | MFCD06659656 |
InChI Key : | WYRRTJKOMZONQO-UHFFFAOYSA-N |
Pubchem ID : | 10607144 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302+H312-H315-H319-H331-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338-P311 |
Class: | 6.1 |
UN#: | 3439 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
93.7% | With ethylenediamine; In glycerol; at 90℃; for 0.25h;Inert atmosphere; | General procedure: To a stirred suspension of 6-nitrobenzothiazole (1b) or <strong>[58249-61-9]6-cyanobenzothiazole</strong> (1c) (5.0 mmol) in glycerol (2.5-3.0 g) under nitrogen, ethylenediamine (12.5 mmol) was added and heated at 90-100 C for 10-15 min. The reaction mixture was diluted with deoxygenated water, cooled under nitrogen to 5-10 C and made acidic(pH 2-3) with concd. HCl. The resulting precipitate was filtered,washed with cold water, and dried under vacuum over KOH giving purethiophenoles 2b and 2c. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; ammonium chloride; In tetrahydrofuran; hexane; | (1) Synthesis of 1-(2,4-difluorophenyl)-1-(6-cyanobenzothiazol-2-yl)-2-chloroethanol STR113 After <strong>[58249-61-9]6-cyanobenzothiazole</strong> (1.60 g) was dissolved in tetrahydrofuran (80 ml), and the solution was cooled to -98 C. in a nitrogen atmosphere, a 1.6M solution (5.9 ml) of n-butyllithium in hexane was added dropwise over 10 minutes, and the resultant mixture was stirred for 5 minutes. A solution of 2-chloro-2',4'-difluoroacetophenone (2.85 g) in tetrahydrofuran (20 ml) was added dropwise to this mixture. After the liquid reaction mixture was heated to -10 C., an aqueous solution of ammonium chloride was added thereto. After the mixture was heated to room temperature, an organic layer was taken out, and the solvent was distilled out under reduced pressure. A water layer was extracted with ethyl acetate and the extract was then put together with the residue of the organic layer. This organic layer was washed with water and then with saturated saline, dried over magnesium sulfate and then distilled under reduced pressure. The residue was subjected to column chromatography on silica gel (solvent: hexane/ethyl acetate=20/1, next, hexane/ethyl acetate=5/1), thereby obtaining the intended compound (1.49 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate; for 4h;Heating / reflux; | A solution of 1,3-benzothiazole-6-carboxamide (1.96 g) in POCl3 (10 ml) was refluxed for 4 hours. The reaction solution was concentrated, and water was slowly added thereto at 0C. It was extracted with EtOAc, and the organic layer was dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20 to 60:40) to obtain 1,3-benzothiazole-6-carbonitrile as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With copper(l) iodide; palladium(II) trifluoroacetate; potassium carbonate; tricyclohexylphosphine; In 5,5-dimethyl-1,3-cyclohexadiene; at 140℃; for 12h;Inert atmosphere; | General procedure: 1 mL Xylene was added into the flask charged with 0.25 mmol 4-quinolinonyl triflate, 0.75 mmol benzothiazole, 5 mol% Pd(TFA)2 (4.1 mg), 20 mol% PCy (14 mg), 0.25 mmol K2CO3, 10 mol% CuI (4.7 mg). The mixture was stirred at 140oC under Ar for 12 hours, then cooled down to room temperature, diluted with 20 mL ethyl acetate and washed with 10 mL H2O. The aqueous layer was extracted twice with ethyl acetate (5 mL) and the combined organic phase was dried over Na2SO4. After evaporation of the solvents the residue was purified by flash column chromatography (silica gel, PE/EtOAc) to afford the desired products 3 and 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With water; caesium carbonate; for 0.166667h;Microwave irradiation; | General procedure: Add 2 ml of water to the microwave reactor,1 mmol of benzothioamide and 0.2 mmol of cesium carbonate,Reacted at a fixed power of 120 W for 10 min,Extracted with ethyl acetate and concentrated under reduced pressure.To give a pale yellow solid, yield 99%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.9% | General procedure: To a stirred suspension of 6-nitrobenzothiazole (1b) or<strong>[58249-61-9]6-cyanobenzothiazole</strong> (1c) (10 mmol) in glycerol (5 g) under nitrogen,ethylenediamine (25 mmol) was added and heated at 90-100 C for10-15 min. The reaction mixture was poured onto ice-water mixture(200 ml), 1.0 ml of 30% H2O2 was added dropwise and stirred at 5 Cfor 30 min. The resulting precipitate was filtered, washed with water,and air-dried giving pure disulfides 3b and 3c. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With tert.-butylhydroperoxide; N-chloro-succinimide; In decane; dimethyl sulfoxide; at 120℃; for 10h;Schlenk technique; | Weigh out benzaldehyde (0.37 mmol, 39.6 mg), 5-chloro-benzothiazole (1.0 eq., 0.37 mmol, 59.2 mg), NCS (40 mol%, 0.15 mmol, 20.1 mg) and 5.5 M TBHP in decane ( 2.5 eq., 0.93 mmol, 169 muL) in a 25 mL Schlenk reaction tube, then add DMSO (30 eq., 11.1 mmol, 0.86 g), and place the reaction at 120 C. After 15 h, the reaction was completed. After extraction, the organic layer was concentrated to remove the solvent, and the concentrated solution was separated by column chromatography (eluent is a petroleum ether-ethyl acetate mixed solvent with a volume ratio of 1: 1) to obtain a white solid, namely the derivative Iv. The yield is 12%. |
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