Structure of 3704-41-4
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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. : | 3704-41-4 |
Formula : | C9H6N2O2S |
M.W : | 206.22 |
SMILES Code : | O=[N+](C1=CC=C(C2=NC=CS2)C=C1)[O-] |
MDL No. : | MFCD26794836 |
InChI Key : | LGDOGDJADXLHLA-UHFFFAOYSA-N |
Pubchem ID : | 13546655 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H320-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
58.6% | With sulfuric acid; nitric acid; In water; at 0℃; for 1h; | A solution of 2-phenyl thiazole (200mg, 1.24mmol) in cone, sulphuric acid (0.5ml) was cooled to O0C. The nitrating mixture (made up of 0.5ml of cone, nitric acid and 0.5ml of cone, sulfuric acid) was added dropwise and stirred at O0C for lhr. The reaction was quenched with ice water and basified with sodium hydroxide solution. The resultant precipitate was filtered and washed with water. Purification by column chromatography over silica gel using EtOAc/ pet ether gave 2-(4-nitrophenyl) thiazole (150mg, 58.6%) as solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With iron; In acetic acid; at 20℃; for 2h; | Iron powder (0.5g, 8.92mmol) was added portion wise to a solution of 2-(4- nitrophenyl)-thiazole (200mg, 0.97mmol) in acetic acid (5ml) and stirred at room temperature for 2hr. The reaction mixture was diluted with water, basified with dilute sodium hydroxide, filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with water, brine and dried. Evaporation of the solvent yielded 4- thiazol-2-yl-phenylamiiie (150mg, 88%) as solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N'-disalicylideneethylenediamine; caesium carbonate;copper(l) iodide; cobalt(II) acetate; In 1,4-dioxane; at 150℃; for 10h; | Preparation of 4-[2-(4-Nitro-phenyl)-6-oxo-4-thioxo-6H-1-thia-3,3b,5-triaza-cyclopenta[a]pentalen-5-yl]-butyric acid ethyl ester (Compound 37) As depicted in Scheme 24 below, anhydrous Co(OAc)2 (0.021 mmol, 5%) and SALEN (2,2'-(1,4-diiminobutane-1,4-diyl)diphenol, 0.041 mmol, 0.1 molequivalent) in 0.5 ml dry dioxane are placed in a flame-dried flask, and the mixture is stirred for 10 minutes at room temperature. A solution of thiazole (0.411 mmol) in 1 ml dry dioxane, anhydrous Cs2CO3 (0.493 mmol, 1.2 molequivalents) and CuI (0.822 mmol, 2 molequivalents) are thereafter added consecutively to the reaction mixture under argon. A solution of 4-nitrophenyl iodide (0.493 mmol, 1.2 molequivalents) in dry dioxane (0.5 ml) is then added dropwise and the resulting mixture is heated to 150 C. under argon, while monitoring the reaction progress by TLC. Once the reaction is completed (after about 10 hours), the resulting mixture is diluted with chloroform (20 ml) and filtered through a celite pad. The organic solvents are evaporated under reduced pressure and the crude product is purified by flash column chromatography, using a hexane:ethyl acetate mixture as eluent, to give pure 2-[4-nitrophenyl]thiazole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
As depicted in Scheme 25 below, <strong>[3704-41-4]2-(4-nitrophenyl)thiazole</strong> (19.9 mmol) dissolved in ether (20 ml) is added dropwise over 1 hour to a stirred and cooled (-78 C.) solution of butyl lithium (1.5 M) in n-hexane (20 ml, 29.9 mmol), diluted with ether (50 ml). The mixture is stirred at -78 C. for 30 minutes and then a solution of N-formylmorpholine (29.9 mmol) in ether (30 ml) is added dropwise over a time period of 15 minutes. After 30 minutes at -78 C., the mixture is washed with saturated aqueous NaHCO3 (30 ml) and extracted with ether (2*20 ml). The organic phase is dried over Na2SO4 and the solvent is removed under reduced pressure to give the crude <strong>[3704-41-4]2-(4-Nitro-phenyl)-thiazol</strong>e-5-carbaldehyde. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.00% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; toluene; at 80℃; for 12h;Inert atmosphere; | A mixture of 4-nitrophenyl)boronic acid (23.00 g, 137.78 mmol, 1.00 eq.), 2-bromothiazole (25.54 g, 155.69 mmol, 14.03 mL, 1.13 eq.), Na2C03 (36.51 g, 344.45 mmol, 2.50 eq.) and Pd(dppf)Cl2.CH2Cl2 (6.75 g, 8.27 mmol, 0.06 eq.) in Tol. (250.00 mL)/H20 (100.00 mL)/dioxane (250.00 mL) was degassed and purged with N2 for 3 times. The mixture was stirred at 80C for 12 hrs under N2 atmosphere and LCMS showed the reaction was complete. The mixture was concentrated and the residue was purified by column chromatography (Petroleum ethenEthyl acetate=50: l to 5: 1) to give 2-(4-nitrophenyl)thiazole (14.00 g, 67.89 mmol, 56.00% yield) as a yellow solid. 1H NMR (400MHz, CHLOROFORM-d) delta = 8.35 - 8.29 (m, 2H), 8.21 - 8.12 (m, 2H), 7.99 (d, J = 3.2 Hz, 1H), 7.50 (d, J = 3.2 Hz, 1H). |
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