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CAS No. : | 2942-15-6 | MDL No. : | MFCD01325556 |
Formula : | C8H7NS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IVKILQAPNDCUNJ-UHFFFAOYSA-N |
M.W : | 149.21 | Pubchem ID : | 3745455 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.59 |
TPSA : | 41.13 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.53 cm/s |
Log Po/w (iLOGP) : | 2.08 |
Log Po/w (XLOGP3) : | 2.37 |
Log Po/w (WLOGP) : | 2.6 |
Log Po/w (MLOGP) : | 1.84 |
Log Po/w (SILICOS-IT) : | 3.65 |
Consensus Log Po/w : | 2.51 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.92 |
Solubility : | 0.178 mg/ml ; 0.00119 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.87 |
Solubility : | 0.199 mg/ml ; 0.00134 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.34 |
Solubility : | 0.0687 mg/ml ; 0.00046 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.74 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
Thiazoles (1b-f, j) were prepared from 2-aminothiazoles according to the reported procedure with slight modifications. 24 To a mechanically-stirred solution of 2-amino-6-chlorobenzothiazole (4 g, 21.7 mmol, 1.0 equiv) in 84% aq phosphoric acid (80 mL) was added a solution of sodium nitrite (9.0 g, 13 mmol, 6.0 equiv) in water (28 mL) dropwise below the surface at -10 C. After stirring at -10 C for another 2 h, a 50% aq solution of hypophosphorous acid (60 mL) was added dropwise to the resulting thick syrup mixture at -5 C. The reaction mixture was warmed to room temperature, stirred overnight, and then diluted with water (300 mL). Na2CO3 was added portionwise to adjust to pH=8 and extracted with DCM. The organic phase was dried over Na2SO4, concentrated under vacuum, and purified over column chromatography (petroleum ether/EtOAc=100:1) to give 6-chlorobenzothiazole as white solid (2.2 g, 59% yield). | ||
With isopentyl nitrite; In tetrahydrofuran; for 0.5h;Reflux; | General procedure: A 50 mLSchlenk tube was charged with 2-aminobenzothiazole derivative (6.5 mmol) and 10mL of THF, and then isoamyl nitrite (14.3 mmol) was added slowly into thesolution. The resultant mixture was refluxed for 30 minutes, and poured intoice-water, and the resultant aqueous mixture was extracted with ethyl acetate(3×30 mL). The organic extracts were combined and washed with brine, dried overMgSO4, filtered, concentrated in vacuum andpurified by column chromatography, giving the desired benzothiazoles in similaryields with the reported procedure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With n-butyllithium; In tetrahydrofuran; | (1) 2-Acetyl-<strong>[2942-15-6]6-methylbenzothiazole</strong> A solution of <strong>[2942-15-6]6-methylbenzothiazole</strong> (6.1 g, 41 mmol) in anhydrous THF (150 ml) was cooled to -78 C. To the cooled solution was added, with stirring, n-butyl lithium (28.1 ml of 1.6 M n-BuLi-containing hexane solution, 45 mmol) dropwise under nitrogen atmosphere. Further, a solution of N,N-dimethyl acetamide (3.9 g, 45 mmol) in anhydrous THF (70 ml) was added dropwise to the mixture at the same temperature. After completion of the addition, the mixture was stirred for an hour, and then warmed to room temperature. The reaction mixture was poured into water, and then extracted with benzene. The extract was washed with water, dried over magnesium sulfate, and then evaporated. The resulting residual powders were subjected to purification using column chromatography on silica gel (eluant, n-hexane/ethyl acetate=95/5) to afford 2-acetyl-<strong>[2942-15-6]6-methylbenzothiazole</strong> (3.7 g, 47%) as a pale yellow powder, together with the starting material (2.5 g). NMR(CDCl3) delta: 2.53 (3H, s), 2.81 (3H, s), 7.39 (1H, d, J=1.6 Hz, 8.6 Hz), 7.76 (1H, d, J=1.6 Hz), 8.06 (1H, d, J=8.6 Hz); mp 105-106 C. (n-hexane) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | 0.05 mole of <strong>[2942-15-6]6-methylbenzothiazole</strong> was added to 20 ml of ethyl ether at a temperature ranging -65 to -55 C. On the other hand, 0.05 mole of n-butyl lithium was added to 155 ml of ethyl ether. The former mixture was added to the latter one in a dropwise fashion for 15 minutes. In addition, 0.05 mole of triphenyl bromosilane was added to 20 ml of ethyl ether. The solution was added to the above mixed solution in a dropwise fashion at -45 C. for 5 minutes. The resulting product was heated to -13 C. for 4 hours and also, maintained at a temperature ranging -13 to -10 C. for 4 hours. Then, an aqueous ammonium chloride solution and ice were put in the solution, separating an ethyl ether layer. The separated ethyl ether layer was washed with water, dried with sodium sulfate, and treated under reduced pressure to remove a solution. The resulting semi-solid phase material was extracted with 300 ml of boiling petroleum ether and then treated under reduced pressure to remove a solution. When the solution was removed, the extract was washed with 50 ml of ethanol and 15 ml of benzene and then, recrystallized with a mixture of 6 ml of benzene and 15 ml of ethanol to thereby produce a yellow solid at a yield of 24%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With hydridotetakis(triphenylphosphine)rhodium(I); 1,2-bis-(diphenylphosphino)ethane; In chlorobenzene; for 3h;Inert atmosphere; Reflux; | General procedure: In a two-necked flask equipped with a reflux condenser were placed RhH(PPh3)4 (4 mol%, 11.5 mg), 1,2-bis(diphenylphosphino)ethane (8 mol%, 8.0 mg), 1,3-benzothiazole 5 (0.25 mmol, 27.3 mL), and (alpha-phenylthio)isobutyrophenone 6 (0.25 mmol, 64.0 mg) in chlorobenzene (0.25 mL) under an argon atmosphere, and the solution was heated at reflux for 3 h. The mixture was purified by flash column chromatography on silica gel giving 7 (55.8 mg, 92%) and isobutyrophenone 8 (34.3 mg, 93%) with the recovery of 5 (3.5 mg, 10%) and 6 (0.8 mg, 1%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With palladium diacetate; copper(II) dipivaloate; caesium carbonate; copper(I) bromide; In 1,4-dioxane; dimethyl sulfoxide; at 110℃; for 12h;Schlenk technique; Inert atmosphere; | General procedure: A flame-dried 25-mL Schlenk flask equipped with a magnetic stir bar was charged with Pd(OAc)2 (11.2 mg, 0.05 mmol, 10 mol %), copper(II) pivalate (400 mg, 1.5 mmol, 3.0 equiv), Cs2CO3 (163 mg, 0.5 mmol, 1.0 equiv), pyridine N-oxide (190 mg, 2.0 mmol, 4.0 equiv), and CuBr (7 mg, 0.05 mmol, 10 mol %). The flask was fitted with a rubber septum, evacuated, and refilled with argon (repeating three times). Dioxane/DMSO (19:1, 4.0 mL) and benzothiazole (67.3 mg, 0.5 mmol, 1.0 equiv) were added via syringes under an atmosphere of N2. The septum was then replaced by a Teflon-coated screw cap under N2. The reaction mixture was stirred at room temperature for 15 min and then in a preheated oil bath (at 110 C) for 12 h, cooled down to room temperature, diluted with DCM (15 mL) and filtered through a Celite pad. The filtrate was then washed twice with 10-20 mL of DCM. The combined organic extracts were washed with 5 mL of saturated NH4Cl aq solution (containing 1% v/v ammonium hydroxide) to remove the residual copper(II). The blue aqueous phase was extracted with DCM (15 mL×3). The combined organic phase was dried over Na2SO4, concentrated under vacuum, and purified by column chromatography on silica gel (eluent: DCM/acetone=20:1) to provide the desired product 3a as a pale yellow solid (75 mg, 67% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With iron(III) chloride hexahydrate; oxygen; tricyclohexylphosphine tetrafluoroborate; In water; dimethyl sulfoxide; at 120℃; for 20h; | General procedure: A 10 mL reaction tube was charged with FeCl3·6H2O (2.7 mg, 0.01 mmol), P(Cy)3·HBF4 (3.7 mg, 0.01 mmol), benzothiazole (1a, 21.8 muL, 0.2 mmol), acetophenone (2a, 35 muL, 0.3 mmol), HO 2(0.1 mL) and DMSO (0.3 mL). The reaction vessel was flushed with oxygen for three times and sealed. The resulting solution was heated to 120 oC for 20 h. After cooling to room temperature, the volatiles were removed under vacuum and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 98:2) to give 3a as a yellow solid; yield: 35.9 mg (75%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I) iodide; potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 3h; | General procedure: The following provide the typical experimental procedure for the direct C-H thiolation ofbenzothiazole with thiophenol. To the 5 mL of test tube containing a magnetic stirrer bar was placed(IPr)CuI (29 mg, 0.05 mmol) and K2CO3 (69mg, 0.50 mmol)and subsequently added benzothiazole(mg, 0.25 mmol)thiophenol (mg, 0.50 mmol) in DMF (1.5 mL). The resulting mixture was heated at140 C for 3h. After the mixture was allowed to cool to room temperature, water (1 mL) was addedand the solution was extracted with three portions of 10 mL ethyl acetate. GC/MS analysis revealedthe presence of 2-phenylthiobenzothiazole. The organic layer was dried (MgSO4), filtered, and thesolvent was removed by rotary evaporator in vacuo. The residue was subjected to preparative TLC(hexane/ethyl acetate = 5/1) to give the pure product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With dipotassium peroxodisulfate; iron(III) chloride hexahydrate; In water; dimethyl sulfoxide; at 100℃; for 12h; | General procedure: A dried reflux tube equipped witha magnetic stir bar charged with benzothiazole derivative (0.5 mmol 1.0equiv), benzylalcohol derivative (1.5mmol 3.0equiv), FeCl3·6H2O (0.1equiv), K2S2O8 (2.0 equiv), DMSO/H2O (2:1 mL) and the reaction vessel was placedin a 100C oil bath for 12 h under air. After cooling to room temperature,the mixture was diluted with ethyl acetate and directly filtered through a padof celite and washed with water. The organic phase was dried over NaSO4and removed under reduced vacuum. The residue was purified by columnchromatography eluting with ethyl acetate and hexane to afford thedesired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dipotassium peroxodisulfate; iron(III) chloride hexahydrate; In water; dimethyl sulfoxide; at 100℃; for 12h; | General procedure: A dried reflux tube equipped witha magnetic stir bar charged with benzothiazole derivative (1 mmol 2.0 equiv), acetophenone derivative (0.5 mmol 1.0equiv),FeCl3·6H2O (0.2equiv), K2S2O8 (3.0 equiv), DMSO/H2O (2:1 mL)and the reaction vessel was placed in a 100C oil bath for 12 h under air.After cooling to room temperature, the mixture was diluted with ethyl acetateand directly filtered through a pad of celite and washed with water. Theorganic phase was dried over NaSO4 and removed under reduced vacuum.The residue was purified by column chromatography eluting with ethyl acetateand hexane to afford the desired product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With tert.-butylhydroperoxide; copper dichloride; In water; at 80℃; for 24.5h;Inert atmosphere; Schlenk technique; | General procedure: A 25 mL reaction vessel was charged with benzothiazole 1 (1.86 mmol, 1.1 equiv), aldehyde 2 (1.69 mmol), CuCl2 (0.51mmol, 0.3 equiv), and tert-butylhydroperoxide (2.36 mmol, 1.4 equiv, 70% aqueous solution) under nitrogen. The reactionmixture was stirred in an ice bath for 30 min, and then stirred at 80C for 24 h. After cooling to room temperature, the mixture was purified by column chromatography using silica gel (petroleum ether/ethyl acetate) to afford the products 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | General procedure: A tube-type Schlenk flask was charged with 0.045 mmol of catalyst D, 0.045 mmol of 1,8-diazabicyclo[5.4.0]undec-7-ene (7muL), and 1mL of N-methylpyrrolidone. The solution was stirred under nitrogen atmosphere at 60-70C for 30 min. And, 2mL of N-methylpyrrolidone was added, followed by addition of a balloon charged with carbon dioxide gas. The solution was stirred at 60-70C for 30 min. Then, 2-aminobenzenethiol derivatives (0.5 mmol), phenylsilane (1.5 mmol) dissolved in 0.5mL of N-methylpyrrolidone was added to the mixture. Reaction was carried out at 60-70C for 18-30h. After the solution was cooled to room temperature, purification by flash chromatography on silica gel with n-hexane and ethyl acetate afforded benzothiazole derivatives. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With C11H16N2O2; copper; caesium carbonate; at 80℃; for 14h;Sealed tube; | The 149mg (1mmol) 6- methyl-benzothiazole, 534 (1.8mmol) 1- bromo-2-iodo toluene, 6.4mg (0.1mmol) Cu, 21mg (0.1mmol) ligand L3,978mg (3mmol) Cs2CO3, 2gPEG-200, was added 10mL reaction tube, sealed, under the reaction condition of 80 14h.After the reaction was stopped, extraction with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, column chromatography was purified by silica gel column to give 3,7-dimethyl-phenothiazine 150mg, yield 66%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With N-methoxy-1H-pyrrole-2-carboxamide; copper(ll) sulfate pentahydrate; caesium carbonate; at 100℃; for 14h;Sealed tube; | The 149mg (1mmol) 6- methyl-benzothiazole, 317 (1mmol) 2- bromo-4-chloro-l-iodobenzene, 12.5mg (0.05mmol) CuSO4·5H2O28mg(0.2mmol)L1978mg(3mmol)Cs2CO3, 1gPEG-600, was added 10mL reaction tube, sealed and reacted at 100 14h.After the reaction was stopped, extraction with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, column chromatography was purified by silica gel column to give 2-chloro-7-methyl-phenothiazine hydrochloride 198mg, 80% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With N-methoxy-1H-pyrrole-2-carboxamide; caesium carbonate; copper(II) oxide; at 60℃; for 14h;Sealed tube; | The 149mg (1mmol) 6- methyl-benzothiazole, 317 (1mmol) 2- bromo-4-fluoro-1-iodobenzene, 16mg (0.2mmol) CuO, 28mg (0.2mmol) ligand L1,978mg (3mmol) Cs2CO3, 1gPEG-400, was added 10mL reaction tube, sealed, reaction at 60 for 14h.After the reaction was stopped, extraction with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, column chromatography was purified by silica gel column to give 2-fluoro-3-methyl-phenothiazine piperazine 208mg, yield 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With C11H16N2O2; copper; caesium carbonate; at 70℃; for 14h;Sealed tube; | The 149mg (1mmol) 6- methyl-benzothiazole, 534 (1.8mmol) 4- bromo-1-iodo-toluene, 6.4mg (0.1mmol) Cu, 21mg (0.1mmol) ligand L3,978mg (3mmol) Cs2CO3, 1gPEG-400, was added 10mL reaction tube, sealed, under the reaction conditions of 70 14h.After the reaction was stopped, extraction with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, column chromatography was purified by silica gel column to give 2,7-dimethyl-phenothiazine 148mg, yield 65%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With dipotassium peroxodisulfate; eosin y; at 20℃; for 48h;Schlenk technique; Irradiation; | 6-Methylbenzothiazole (0.5 mmol), K2S2O8 (4 eq.) and Eosin Y (1.4 mol%) were weighed into a 25 mL Schlenk reaction tube, followed by N,N-dimethylacetamide (4.375 g). , 50 mmol), under air, placed under a 20 W LED white light, stirred at room temperature, monitored by TLC, after 48 h, the reaction was completed, the solvent was removed, and the concentrate was separated by column chromatography (petroleum ether) /ethyl acetate = 3 : 1, V / V) A yellow oil was obtained, that is, the derivative Ij. The yield was 87%. |
81% | With dipotassium peroxodisulfate; eosin y; at 20℃; for 22h;Schlenk technique; | Weigh <strong>[2942-15-6]6-methylbenzothiazole</strong> (0.5mmol, 75mg), K2S2O8 (1.5mmol, 0.41g) and Eosin Y (0.0075mmol, 4.9mg) in a 25mL Schlenk reaction tube,Then add N, N-dimethylacetamide (62.5mmol, 5.4g), put it under the LED white light of 15W power to react, stir the reaction at room temperature, monitor the progress of the reaction by TLC, the reaction ends after 22h, the reaction solution The solvent was removed by concentration, and the concentrated solution was separated by column chromatography (eluent: petroleum ether / ethyl acetate with a volume ratio of 3: 1) to obtain a yellow oil, that is, the derivative Ij. Yield was 81%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium phosphate; 1,3-bis-(diphenylphosphino)propane; palladium(II) bromide; In N,N-dimethyl-formamide; at 75℃; for 30h;Green chemistry; | A 2-arylbenzothiazole compound preparation method, the method is to successively add <strong>[2942-15-6]6-methylbenzothiazole</strong>, di(4-bromophenyl)iodonium tetrafluoroborate, palladium bromide, 1,3-bis(diphenylphosphino)propane and potassium phosphate into reaction solvent N,N-dimethylformamide. At 75 C, react for 30 hours.Wherein: bromination arrowhead with 6 - methylbenzothiazol molar ratio of 1:80, 6 - methyl thiazole with b (4 - bromophenyl) four boron fluoride Iodized salt molar ratio of 1: 2.0, 6 - methylbenzothiazol with double (diphenylphosphine) propane 1, 3 - molar ratio of 1:80, 6 - methyl thiazole with potassium phosphate molar ratio of 1: 2.0, 6 - methyl thiazole with N, N - dimethyl formamide in a molar ratio of 1:280.The whole reaction process according to the embodiment 1 of the thin-layer chromatography tracking obtained reaction liquid; the reaction solution according to the embodiment 1 the method sequentially through the extraction, drying, concentration, after the column chromatography, to obtain 6-methyl-2-(4-bromophenyl)benzothiazole, yield is 80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With caesium carbonate; copper(II) oxide; at 140℃; for 24h;Inert atmosphere; | At room temperature, the iodobenzene (0.4mmol, 1 equiv), selenium (1.2mmol, 3 equiv), 6 - methylbenzothiazol (0.8mmol, 2 equiv), CuO (0.04mmol), cesium carbonate (1.2mmol, 3 equiv) is added to the reaction tube, and then the nitrogen, and replace the three times, the reaction environment under nitrogen, then adding the reaction solvent 2 ml DMI, in the 140 C the reaction temperature under stirring 24h. By thin-layer chromatographic monitoring after the reaction, the reaction mixture is cooled, then adding ethyl acetate dilution, the diluted solution in the transfer to the separatory funnel, saturated salt water for extraction, the aqueous phase and the organic phase separated, then the ethyl acetate extract the aqueous phase 3 times, merge all organic phase (namely the saturated salt water extraction and separation of the organic phase and the ethyl acetate extraction and separation of the organic phase), adding 5g anhydrous sodium sulfate, stirring 5 minutes after the filtering, the filter cake washing 3 times, for each time 5 ml ethyl acetate wash, then evaporate the solvent, column chromatography (petroleum ether and ethyl ether volume ratio 100:1 mixture as eluant, silica gel as 300 - 400 mesh silica gel) product is obtained after the 5 - nitro -2 - (benzene selenium) benzothiazole, state, yield 85%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | General procedure: Under an air atmosphere, a sealable reaction tube with a Teflon-coated screw cap equipped with a magnetic stir bar was charged with benzothiazole 1 (1.0 mmol), toluene derivative 2 (3.0 mmol), and Cu(OTf)2 (0.10 mmol) in DCE/DMSO (5:1, 2.0 mL). To this was added 70% aq TBHP (6.0 equiv) at r.t. The rubber septum was then replaced by a Teflon-coated screw cap, and the reaction vessel placed in an oil bath at 90 C for 24 or 36 h. When the reaction was complete, it was cooled to r.t. and monitored by TLC. To the resulting solution was added 98% hydrazine hydrate (0.5 or 1.0 mL), K2CO3 (3.0 mmol), and EtOH(2.0 mL), the mixture was stirred for 5 min and then poured into 10% HCl (15 mL); the mixture was extracted with EtOAc (2 ×). The combined organic layers were dried (anhyd Na2SO4) and the solvents were removed in vacuo. The residue was purified by flash chromatography (silica gel, petroleum ether/EtOAc 20:1) to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.1% | With bis(benzonitrile)palladium(II) dichloride; 1,10-Phenanthroline; 1-aza-4,6,11-trioxa-5-boratricyclo[3.3.3.0(1,5)]undecane; diisopropylamine; In water; dimethyl sulfoxide; butan-1-ol; at 80℃; for 6h; | To a suitable amount of three-component solvent (dimethylsulfoxide (DMSO) in a volume ratio of 6: 1: 1, a mixture of H2O and n-butanol at room temperature) was added 100 mmol of the compound of the above formula Compound and 200 mmol of compound of formula (II) were added and then 7 mmol of catalyst Pd (PhCN) 2 Cl2, 130 mmol of base diisopropanolamine and 18 mmol of promoter (3.6 mmol of 1,10-phenanthroline and 14.4 mmol of triethanolamine boronic acid Ester mixture); the temperature was raised to 70 C and the reaction was stirred at this temperature for 8 hours.After the reaction is completed, the reaction system is naturally cooled to room temperature, sufficient deionized water is added enough to wash 2-3 times, and then extracted with enough chloroform, thoroughly shaken, the upper organic phase is taken, dried over anhydrous sodium sulfate, filtered, The resulting residue was subjected to a pressure distillation over 300-400 mesh silica gel column chromatography using a 2: 1 by volume mixture of acetone and ethyl acetate as the elution solvent to obtain the compound of the formula (III) in a yield of 95.7 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With dipotassium peroxodisulfate; eosin y; at 20℃; for 20h;Schlenk technique; Irradiation; | 6-Methylbenzothiazole (0.5 mmol), K2S2O8 (4 eq.) and Eosin Y (0.5 mol%) were weighed into a 25 mL Schlenk reaction tube, followed by N,N-dimethylpropanamide (8.887 g). , 87.5 mmol), placed under air condition, placed under 15 W LED white light, stirred at room temperature, monitored by TLC, after 20 h, the reaction was completed, the solvent was removed, and the concentrate was separated by column chromatography (petroleum ether) /ethyl acetate = 5 : 1, V / V) gave a yellow oil, the derivative In. The yield was 83%. |
80% | With dipotassium peroxodisulfate; eosin y; at 20℃; for 24h;Schlenk technique; Irradiation; | 6-methylbenzothiazole (0.5 mmol), K2S2O8 (4 eq.) and Eosin Y (0.5 mol%) were weighed into a 25 mL Schlenk reaction tube.Further adding N,N-dimethylpropanamide (3.809 g, 37.5 mmol), under air,The reaction was placed under a 15 W LED white light, and the reaction was stirred at room temperature.The monitoring was carried out by TLC, and the reaction was completed after 20 h, and the reaction solution was concentrated to remove the solvent.The concentrate was separated by column chromatography (petroleum ether / ethyl acetate = 5 : 1, V / V)Get a yellow oil,InstantBiological Ih. The yield was 80%. |
70% | With dipotassium peroxodisulfate; Eosin Y; at 20℃; for 24h;Schlenk technique; | Weigh 6-methylbenzothiazole (0.5mmol, 75mg), K2S2O8 (2mmol, 0.54g) and Eosin Y (0.01mmol, 6.5mg) into a 25mL Schlenk reaction tube, and then add N, N-dimethylpropane Amide (38mmol, 3.8g), placed under a 20W power LED white light to react, stirred the reaction at room temperature, monitored the progress of the reaction with TLC, the reaction was completed after 24h, the reaction solution was concentrated to remove the solvent, and the concentrated solution was separated by column chromatography (The eluent was petroleum ether / ethyl acetate with a volume ratio of 5: 1) to give a yellow oil, namely the derivative In. The yield was 70%. |
Tags: 2942-15-6 synthesis path| 2942-15-6 SDS| 2942-15-6 COA| 2942-15-6 purity| 2942-15-6 application| 2942-15-6 NMR| 2942-15-6 COA| 2942-15-6 structure
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P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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