Structure of 2942-16-7
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 2942-16-7 |
Formula : | C8H7NS |
M.W : | 149.21 |
SMILES Code : | CC1=CC=C(SC=N2)C2=C1 |
MDL No. : | MFCD06659659 |
InChI Key : | SEBIXVUYSFOUEL-UHFFFAOYSA-N |
Pubchem ID : | 14344564 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-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 |
---|---|---|
96% | 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 |
---|---|---|
With N-Bromosuccinimide; In tetrachloromethane; hexane; dichloromethane; | EXAMPLE M 5-Bromomethylbenzothiazole A mixture of <strong>[2942-16-7]5-methylbenzothiazole</strong> (5.0 g), N-bromosuccinimide (6.0 g) and carbon tetrachloride (500 ml) was refluxed for 4 hours. Upon cooling, the mixture was evaporated to dryness and the residue chromatographed over silica gel. On elution with a mixture of methylene chloride and hexane (9:1), the title product was obtained as a white solid [0.56 g; NMR(CDCl3,60 MHz): 4.6 (s, 2H), 7.4 (dd, J=7 Hz, 2 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57%; 55% | At room temperature, (Rs) imine 2 (0.3 mmol) and the additive (0.315 mmol) was dissolved in 3 mL THF with vigorous stirring for about half an hour. The resulted clear solution was added to the priorly prepared benzothiazol-2-yl metallic reagent (0.45 mmol in 3 mL THF) at -78 C. The reaction was accomplished rapidly within 10 min (monitored by TLC). Then the reaction was quenched with aqueous saturated NH4Cl, extracted with DCM (10 mL × 3), washed by brine (10 mL), dried over Na2SO4, and concentrated under vacuum. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate 3:1-1:1). The diastereoselectivity was determined by 1H NMR analysis of the crude product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
j00303j To a solution of compound B-14 (0.27 g, 1.2 mmol) in tetrahydrofuran (4 mL) at -70 C under nitrogen was added n-butyllithium (0.6 mL, 2.5 molL in hexane, 1.5 mmol). The mixture was stirred at -70 C for 0.5 hours. Then a solution of N-bromosuccinimide(0.26 g, 1.5 mmol) in tetrahydrofuran (2 mL) was added at -70 C, and stirring was continued for an additional 0.5 hours. The mixture was quenched with saturated aqueous ammonium chloride (1.2 mL) at -70 C, then diluted with ethyl acetate (200 mL) at 0 C, washed with brine (6 x 10 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by prep-TLC [silica gel, petroleum ether ethyl acetate = 15:1, Rf= 0.52j to give compound B-15 (80 mg, 25% yield, 88% purity) as a yellow solid. ‘H-NMR (CDC13, 400 MHz): 7.79 (s, 1H), 7.68 (d, J=8.0 Hz, 1H), 7.26 (d, J=11.2 Hz, 1H), 2.51 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); In tetrahydrofuran; water; at 15 - 60℃; for 12h;Inert atmosphere; | j00301j A mixture of 5-bromobenzo[djthiazole (0.34 g, 1.6 mmol), 2,4,6-trimethyl-1,3,5,2,4,6- tnoxatnbonnane (0.60 g, 4.8 mmol), dicyclohexyl-[3 -(2,4,6-triisopropylphenyl)phenyljphosphane [2- (2-aminophenyl)phenylj-chloro-palladium; (0.06 g, 0.08 mmol) and potassium phosphate (0.67 g, 3.2 mmol) in tetrahydrofuran (12 mL) and water (3 mL) at 15 C was degassed and purged with nitrogen 3 times. The mixture was stirred at 60 C for 12 hours under nitrogen, then diluted with ethyl acetate (250 mL) and washed with brine (6 x 20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give compound B-14 (0.27 g, 78% yield) as brown gum, which used directly without further purification. LCMS (Y): tR=0.633 mi, (ES) mlz (M+H) = 150.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With scandium tris(trifluoromethanesulfonate); In 1,2-dichloro-ethane; at 20℃; for 72h;Schlenk technique; Sealed tube; Molecular sieve; Inert atmosphere; | To a 10 mL Schlenk tube was added Sc(OTf)3 (4.9 mg, 0.01 mmol, 10 mol%) and activated molecular sieves (60.0 mg). Seal the tube with a threaded rubber plug,Nitrogen was replaced 3 times, and then a solution of <strong>[2942-16-7]5-methylbenzothiazole</strong> 1 g (14.9 mg, 0.1 mmol, 1.0 eq) in DCE (0.5 mL) and phenyl oxirane dissolved in a solution was added at room temperature. Dicarboxylate 2a (52.8 mg, 0.2 mmol, 2.0 eq)A solution of DCE (0.5 ml). The mixture was then stirred at room temperature for 72 hours. The reaction was followed by TLC. After completion of the reaction, ethyl acetate/petroleum ether system (petrole ether/ethyl = 30/1) was used.Purification of the reaction mixture by preparative thin layer chromatography,38.0 mg of colorless oil 3ba was obtained.The yield was 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper(l) iodide; potassium sulfide; ammonium acetate; In water; at 140℃; for 11h;Schlenk technique; Inert atmosphere; | In the dry Schlenk reaction tube, add 2-iodo-5-methylaniline (0.2 mmol), potassium sulfide (0.6 mmol), dimethyl sulfoxide (2 mL), cuprous iodide (0.04 mmol), and acetic acid. Ammonium (1.2 mmol) and water (80 ul). After the sample is added, vacuum with an oil pump and inject nitrogen for gas replacement. After three replacements, the reaction is stopped at 140 for 11 hours and then cooled to room temperature. The reaction is detected by thin-layer chromatography (TLC). After the reaction of the raw materials is completed, the reaction is terminated, and the mixed solution in the reaction tube is cooled to room temperature. Preliminary treatment of the mixed solution: passing through a short column, extracting, collecting the organic layer, spinning powder, and performing column chromatography to obtain the target product with a yield of 85%. |
A574445 [933725-07-6]
Benzo[d]thiazol-5-ylmethanamine
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