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CAS No. : | 2941-72-2 | MDL No. : | MFCD00005795 |
Formula : | C9H9NOS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DYHLJSUORLPGNT-UHFFFAOYSA-N |
M.W : | 179.24 | Pubchem ID : | 76254 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
22% | With boron tribromide In dichloromethane at -78 - 0℃; for 1 h; Inert atmosphere | A 1N boron bromide methylene chloride solution (8.4 ml, 8.40 mmol) was added to a methylene chloride solution (10 ml) of 6-methoxy-2-methylbenzothiazole (500 mg, 2.79 mmol), at -78°C, under nitrogen stream, and stirring was carried out at 0°C for 1 hour. Water was added to the reaction solution, followed by extraction with methylene chloride. The extract was washed sequentially with a saturated aqueous sodium hydrogencarbonate solution and water, and then dried over anhydrous sodium sulfate. The organic layer was concentrated and the resulting residue was purified by a medium-pressure preparative liquid chromatograph (manufactured by Yamazen Corporation, W-Prep 2XY) to afford 2-methyl-1,3-benzothiazol-6-ol (103 mg, yield 22percent) as a colorless oil. 1H-NMR (CDCl3, 400 MHz) δ: 7.66 (1H, d, J=8.8 Hz), 7.23 (1H, d, J=2.4 Hz), 6.94 (1H, dd, J=8.8 Hz, 2.4 Hz), 2.74 (3H, s). MS (ESI, m/z): 166 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; potassium hexacyanoferrate(III) | ||
With sodium hydroxide; potassium hexacyanoferrate(III) | ||
With potassium hydroxide; potassium hexacyanoferrate(III) In water at 80 - 90℃; for 2h; |
With sodium hydroxide; potassium hexacyanoferrate(III) In ethanol; water at 80℃; for 0.5h; | 5. General procedure for the synthesis of 2-methylbenzothiazoles (13a-e) General procedure: The thioamides (12a-e, 10mmol) was wetted with ethanol and dissolved in 8N NaOH. This solution was added to an aqueous solution of K3Fe(CN)6 at 80°C in a drop wise manner. At the completion of the reaction, the solid formed was filtered and used for the following step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogen bromide at 125℃; for 6h; | |
22% | With boron tribromide In dichloromethane at -78 - 0℃; for 1h; Inert atmosphere; | 91.1 A 1N boron bromide methylene chloride solution (8.4 ml, 8.40 mmol) was added to a methylene chloride solution (10 ml) of 6-methoxy-2-methylbenzothiazole (500 mg, 2.79 mmol), at -78°C, under nitrogen stream, and stirring was carried out at 0°C for 1 hour. Water was added to the reaction solution, followed by extraction with methylene chloride. The extract was washed sequentially with a saturated aqueous sodium hydrogencarbonate solution and water, and then dried over anhydrous sodium sulfate. The organic layer was concentrated and the resulting residue was purified by a medium-pressure preparative liquid chromatograph (manufactured by Yamazen Corporation, W-Prep 2XY) to afford 2-methyl-1,3-benzothiazol-6-ol (103 mg, yield 22%) as a colorless oil. 1H-NMR (CDCl3, 400 MHz) δ: 7.66 (1H, d, J=8.8 Hz), 7.23 (1H, d, J=2.4 Hz), 6.94 (1H, dd, J=8.8 Hz, 2.4 Hz), 2.74 (3H, s). MS (ESI, m/z): 166 (M+H)+. |
With hydrogen bromide |
With hydrogen iodide | ||
With hydrogenchloride | ||
With boron trifluoride; acetic acid for 24h; Heating; | ||
6 Synthesis of 2-Methylbenzothiazol-6-ol (50) Synthesis of 2-Methylbenzothiazol-6-ol (50) Compound 50 was prepared from the commercially available 6-methoxy-2-methyl-benzothiazole as described in partC-4 of Example 1. | ||
In water; hydrogen bromide; acetic acid | 133.A 6-Hydroxy-2-methyl-benzothiazole Step A 6-Hydroxy-2-methyl-benzothiazole A mixture of 6-methoxy-2-methyl-benzothiazole (2.5 gm, 0.014 mol) in 30% HBr in acetic acid (15 mL) was stirred for 2 days at 70° C. After cooling, the solid was filtered, washed with ether, and dried in vacuo. The solid was taken up in water (20 mL) and neutralized with saturated NaHCO3 solution. The resulting solid was filtered, washed with water, and dried in vacuo at 40° C.; yield 1.2 gm. | |
Stage #1: 6-methoxy-2-methylbenzothiazole With hydrogen bromide In water at 105℃; for 28h; Stage #2: With sodium hydroxide In water at 20℃; | 39.a Example 39{ [l-Cyano-4-hydroxy-6- (2-methyl-benzothiazol-6-yloxy)-soquinoline-3-car bonylj - amino}-acetic acid a) 2-Methyl-benzothiazol-6-ol[0330] A mixture of 6-methoxy-2-methyl-benzothiazole (19.71 g, 0.11 mol), tetrabutylphosphonium bromide (3.73 g, 0.01 mol), and 48% HBr (120 mL) was stirred at 1050C for twenty-eight hours before it was cooled to room temperature, neutralized with ION NaOH (90 mL) and IN NaOH (45 mL) to pH = 4. The resulting precipitate was filtered, washed with water (3 x 100 mL), dried in vacuo to give the title compound as a pale brown solid (14.81 g): 1H NMR (CDCl3, 200 MHz): δ = 7.77 (m, IH), 7.24 (m, IH)5 6.94 (m, IH)5 5.28 (s, IH), 2.79 (s, 3H). | |
6 Synthesis of 2-methylbenzothiazol-6-ol (50): Synthesis of 2-methylbenzothiazol-6-ol (50): Compound 50 was prepared from the commercially available 6-methoxy-2-methyl-benzothiazole as described in partC-4 of Example 1. | ||
Stage #1: 6-methoxy-2-methylbenzothiazole With boron tribromide In dichloromethane at 20 - 78℃; Stage #2: With methanol In dichloromethane | 4.A Step A: Preparation of 2-methylbenzo[d]thiazol-6-ol: To a cooled (-78°C) solution of 6-methoxy-2-methylbenzo[d]thiazole (0.861 g, 4.80 mmol) in dichloromethane (10 mL) was added BBr3 (5 mL of 1.0 M solution in dichloromethane). After slowly warming to room temperature and stirring for 16 hours, the mixture was cooled to 0 °C and slowly quenched with methanol (20 mL). The reaction mixture was warmed to room temperature and concentrated under reduced pressure. The residue was partitioned between saturated NaHCO3 and dichloromethane/isopropyl alcohol (85/15). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to provide the crude product (0.351 g, 44%) that was used without further purification. | |
With boron tribromide In dichloromethane at -78 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-methyl-pyrrolidin-2-one; sodium hydride at 150℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In dimethyl sulfoxide for 24h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; Perbenzoic acid In tetrachloromethane for 14h; Heating; Irradiation; | ||
With N-Bromosuccinimide; Perbenzoic acid In tetrachloromethane for 30h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With disulfur dichloride at 50 - 70℃; Reduktion des Reaktionsprodukts mit Na2S2O4 in waessrig-alkoholischer Natronlauge bei 50grad und Behandlung mit Acetanhydrid in waessrig-alkoholischer Loesung; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: boron trifluoride etherate / 120 °C 2: 82 percent / pyridine / methanol / 15 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-bromosuccinimide, benzoyl peroxide / CCl4 / 30 h / Heating 2: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) DMF, 0 deg C, 2 h 3: 77 percent / conc. HCl, AcOH / 4.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-bromosuccinimide, benzoyl peroxide / CCl4 / 30 h / Heating 2: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) DMF, 0 deg C, 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 50percent aq. sodium hydroxide / dimethylsulfoxide / 24 h / Ambient temperature 2: 52 percent / 12 h / 150 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 99 percent / 48 percent HBr / 6 h / 125 °C 2: 85 percent / NaNO2, conc. HCl / H2O / 1 h / 0 - 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / 48 percent HBr / 6 h / 125 °C 2: 85 percent / NaNO2, conc. HCl / H2O / 1 h / 0 - 5 °C 3: heptane; ethanol / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / 48 percent HBr / 6 h / 125 °C 2: 85 percent / NaNO2, conc. HCl / H2O / 1 h / 0 - 5 °C 3: heptane; ethanol / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / 48 percent HBr / 6 h / 125 °C 2: 85 percent / NaNO2, conc. HCl / H2O / 1 h / 0 - 5 °C 3: 5 percent / heptane; ethanol / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / 48 percent HBr / 6 h / 125 °C 2: 85 percent / NaNO2, conc. HCl / H2O / 1 h / 0 - 5 °C 3: 30 percent / heptane; ethanol / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / 48 percent HBr / 6 h / 125 °C 2: 85 percent / NaNO2, conc. HCl / H2O / 1 h / 0 - 5 °C 3: heptane; ethanol / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / 48 percent HBr / 6 h / 125 °C 2: 85 percent / NaNO2, conc. HCl / H2O / 1 h / 0 - 5 °C 3: 30 percent / toluene / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NBS, benzoyl peroxide / CCl4 / 14 h / Heating; Irradiation 2: NaH / dimethylformamide / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene; phosphorus pentasulfide 2: potassium ferricyanide; diluted NaOH-solution | ||
Multi-step reaction with 2 steps 1: Lawessons reagent / 1,4-dioxane / 3 h 2: sodium hydroxide; potassium hexacyanoferrate(III) / ethanol; water / 0.5 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Br2 / acetic acid / Ambient temperature 2: aq. HCl / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: BF3 / 24 h / Heating 2: NaOEt / ethanol / 1.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: KOH / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10 mg | With hexamethylenetetramine In trifluoroacetic acid for 7h; Heating / reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | 35 (E)-2-[2-(4-Dibutylaminopropoxyphenyl)ethenyl]-6-methoxybenzothiazole EXAMPLE 35 (E)-2-[2-(4-Dibutylaminopropoxyphenyl)ethenyl]-6-methoxybenzothiazole The procedure of Example 28 was followed starting with 4-chloropropoxybenzaldehyde (5.0 g, 25 mmol) and using 6-methoxy-2-methylbenzothiazole (4.2 ml, 25 mmol) in place of 2-methylbenzothiazole to give (E)-2-[2-(4-chloropropoxyphenyl)ethenyl]-6-methoxybenzothiazole (2.5 g, 28% yield) as an amber oil. 1 H NMR (CDCl3): δ 7.44-6.82 (m, 9H9, 4.21 (t, J=5.3 Hz, 2H), 3.93 (s, 3H), 3.41 (t, J=5.3 Hz, 2H), 2.51 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With selenium(IV) oxide; In 1,4-dioxane; | (i) Oxidation of 6-methoxy-2-methylbenzothiazole (10.0 g, 55.9 mmole) with selenium dioxide (6.2 g, 55.9 mmole) in 300 ml dioxane for six hours by the method of Preparation H gave 6.0 g of 6-methoxy-2-formylbenzothiazole after chromatography of the crude product on silica gel, eluding with chloroform. 1 H--NMR(CDCl3)ppm(delta): 3.9 (s, 3H), 7.1-7.5 (m, 2H), 8.0-8.3 (m, 1H), 10.1 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With CO In water; acetic acid byproducts: CH3COOK, HCN(g); 1:1 H2O-AcOH soln. of the benzothiazole added to filtered aq. soln. K3(Cr(NO)(CN)5)*H2O with shaking, resulting green soln. heated (80°C, 30-35 min); CO bubbled through the react. mixt. (few h) to expel liberated HCN, pptn., filtered, washed several times (dil. acetic acid, then water), dried (vac., silica gel), elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 6-methoxy-2-methylbenzothiazole With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; Stage #2: 6-chloropiperonyl chloride In tetrahydrofuran at -78 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: N-(2-iodo-4-methoxyphenyl)acetamide With sodiumsulfide nonahydrate In N,N-dimethyl-formamide at 80℃; for 12h; Schlenk technique; Sealed tube; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20℃; for 10h; | General Procedure for Synthesis of Substituted Benzothiazoles Catalyzedby MCM-41-NHC-CuI General procedure: To an oven-dried Schlenk tube were added Na2S•9H2O (or K2S, 3.0mmol), o-haloanilide (1.0 mmol), and MCM-41-NHC-CuI (228 mg, 0.1 mmol). The tube was sealed and then evacuated and backfilled withargon, and DMF (2 mL) was injected with a syringe. The mixture washeated to 80 C with stirring for 12 h (140 C and 24 h for o-bromoanilide).Upon cooling to ambient temperature, the mixture was centrifugatedto separate the copper catalyst. The catalyst recovered waswashed with deionized water (3 × 2 mL) and acetone (3 × 2 mL) anddried in vacuo at 80 C for 1 h, and used in the next run. Then conc. HCl(0.8 mL) was added into the resultant solution. After stirring for 10 h atambient temperature, 10 mL saturated aq. NaHCO3 was added into thesolution and the resulting mixture was then extracted with EtOAc forthree times. After being washed with water and brine, the organic layerwas dried over anhydrous MgSO4 and concentrated under the reducedpressure. The residue was then purified via column chromatography onsilica gel (hexane/ethyl acetate) to furnish the expected product 2. |
73% | Stage #1: N-(2-iodo-4-methoxyphenyl)acetamide With copper(l) iodide; sodiumsulfide nonahydrate In N,N-dimethyl-formamide at 80℃; for 12h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20℃; | |
Stage #1: N-(2-iodo-4-methoxyphenyl)acetamide With hydrogenchloride; copper(l) iodide; sodiumsulfide nonahydrate In N,N-dimethyl-formamide at 80℃; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | In acetone for 20h; Reflux; | 2.AA 6-Methoxy-2-methylbenzothiazole methiodide (001) 6-Methoxy-2-methylbenzothiazole methiodide (001) Method AA: To a stirred solution of 6-methoxy-2-methylbenzothiazole (1.00 g, 5.58 mmol) in acetone (3 mL) was added iodomethane (1.04 mL, 16.74 mmol) and the solution was stirred at reflux for 20 hours. After cooling to room temperature, the mixture was filtered, and the solid collected was washed with acetone (3*3 mL), to give the crude product as a white, semi-crystalline solid (1.41 g), which was recrystallized from MeOH to give the title compound as white crystals (1.05 g, 59%). 1H-NMR (500 MHz, d-DMSO): 3.10 (s, 3H, CH3C=N); 3.90 (s, 3H, OCH3); 4.15 (s, 3H, NCH3); 7.48 (br d, 1H, J=9.2, Ar-H); 7.99 (br s, 1H, Ar-H); 8.18 (d, 1H, J=9.2, Ar-H). ESI-MS (pos., MeOH): 194 (100, [M-I]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid monohydrate / toluene / 18 h / 110 °C / Sealed tube 2: tin(ll) chloride; hydrogenchloride / water / 1 h / 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: p-toluenesulfonic acid monohydrate / toluene / 18 h / 110 °C / Sealed tube 2.1: tin(ll) chloride; hydrogenchloride / water / 1 h / 45 °C 3.1: hydrogenchloride; sodium nitrite / water; methanol / 0 °C 3.2: 3 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: p-toluenesulfonic acid monohydrate / toluene / 18 h / 110 °C / Sealed tube 2.1: tin(ll) chloride; hydrogenchloride / water / 1 h / 45 °C 3.1: hydrogenchloride; sodium nitrite / water; methanol / 0 °C 3.2: 3 h / 0 - 20 °C 4.1: triethylamine; bis(triphenylphosphino)copper(I) nitrate / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With p-toluenesulfonic acid monohydrate In toluene at 110℃; for 18h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; water / 24 h / Reflux 2: toluene / 80 °C | ||
Multi-step reaction with 2 steps 1: potassium hydroxide; water / 24 h / Reflux 2: toluene / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene at 80℃; | 7 Synthesis of compound 12 To a mixture of compound 10 (0.3 g, 1 .93 mmol) in toluene (4 ml) was added acetyl chloride (compound 11 ) (0.167 g, 2.13 mmol) dropwise in 15 min. After the mixture was heated at 80°C overnight, cooled to room temperature, the mixture was diluted with DCM (20 ml), and the adjusted pH=8 by saturated NaHC03. The organic phase was separated, washed with brine, dried over Na2S04, and concentrated to give the desired crude compound 12 (0.23 g, yield 66%) as yellow oil, used in next step without further purification. HNMR (CDCI3): 57.82(11-1, d, J=8.8Hz), 7.28(1 H, d, J=2.4Hz), 7.04(1 H, dd, J2=2.4Hz), 3.86(3H, s), 2.79(3H, s) | |
In toluene at 80℃; | 7.12 Synthesis of Compound 12 [0223] To a mixture of compound 10 (0.3 g, 1.93 mmol) intoluene ( 4 ml) was added acetyl chloride (compound 11)(0.167 g, 2.13 mmol) dropwise in 15 min. After the mixturewas heated at 80° C. overnight, cooled to room temperature,the mixture was diluted with DCM (20 ml), and the adjustedpH=8 by saturated NaHC03 . The organic phase was separated,washed with brine, dried over Na2S04 , and concentrated to give the desired crude compound 12 (0.23 g, yield66%) as yellow oil, used in next step without further purification.[0224] 1HNMR (CDC13): o7.82 (lH, d, 1=8.8 Hz), 7.28(lH, d, 1=2.4 Hz), 7.04 (lH, dd, 11 =8.8 Hz, 12=2.4 Hz), 3.86(3H, s), 2.79 (3H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4: caesium carbonate / N,N-dimethyl-formamide / 2 h / 130 °C | ||
Multi-step reaction with 4 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: acetic acid; hydrogen bromide / Sealed tube; Reflux 4: cesium carbonate or Cs2O3 / N,N-dimethyl-formamide / 2 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4: caesium carbonate / N,N-dimethyl-formamide / 2 h / 130 °C 5: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C | ||
Multi-step reaction with 5 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: acetic acid; hydrogen bromide / Sealed tube; Reflux 4: cesium carbonate or Cs2O3 / N,N-dimethyl-formamide / 2 h / 130 °C 5: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4: caesium carbonate / N,N-dimethyl-formamide / 2 h / 130 °C 5: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux | ||
Multi-step reaction with 6 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: acetic acid; hydrogen bromide / Sealed tube; Reflux 4: cesium carbonate or Cs2O3 / N,N-dimethyl-formamide / 2 h / 130 °C 5: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: toluene / Reflux 2.1: triethylamine / ethanol / 0.5 h / 105 °C 3.1: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 130 °C 5.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6.1: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 7.2: 0.5 h | ||
Multi-step reaction with 7 steps 1.1: toluene / Reflux 2.1: triethylamine / ethanol / 0.5 h / 105 °C 3.1: acetic acid; hydrogen bromide / Sealed tube; Reflux 4.1: cesium carbonate or Cs2O3 / N,N-dimethyl-formamide / 2 h / 130 °C 5.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6.1: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 7.2: 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: toluene / Reflux 2.1: triethylamine / ethanol / 0.5 h / 105 °C 3.1: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 130 °C 5.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6.1: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 7.2: 0.5 h 8.1: acetic acid; iron / 1 h / 60 °C | ||
Multi-step reaction with 8 steps 1.1: toluene / Reflux 2.1: triethylamine / ethanol / 0.5 h / 105 °C 3.1: acetic acid; hydrogen bromide / Sealed tube; Reflux 4.1: cesium carbonate or Cs2O3 / N,N-dimethyl-formamide / 2 h / 130 °C 5.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6.1: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 7.2: 0.5 h / 20 °C 8.1: iron; acetic acid / 1 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: toluene / Reflux 2.1: triethylamine / ethanol / 0.5 h / 105 °C 3.1: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 130 °C 5.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6.1: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 7.2: 0.5 h 8.1: acetic acid; iron / 1 h / 60 °C 9.1: toluene; chloroform / 2 h / 80 °C | ||
Multi-step reaction with 9 steps 1.1: toluene / Reflux 2.1: triethylamine / ethanol / 0.5 h / 105 °C 3.1: acetic acid; hydrogen bromide / Sealed tube; Reflux 4.1: cesium carbonate or Cs2O3 / N,N-dimethyl-formamide / 2 h / 130 °C 5.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6.1: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 7.2: 0.5 h / 20 °C 8.1: iron; acetic acid / 1 h / 60 °C 9.1: toluene; chloroform / 2 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: toluene / Reflux 2.1: triethylamine / ethanol / 0.5 h / 105 °C 3.1: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 130 °C 5.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6.1: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 7.2: 0.5 h 8.1: acetic acid; iron / 1 h / 60 °C 9.1: toluene; chloroform / 2 h / 80 °C 10.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C | ||
Multi-step reaction with 10 steps 1.1: toluene / Reflux 2.1: triethylamine / ethanol / 0.5 h / 105 °C 3.1: acetic acid; hydrogen bromide / Sealed tube; Reflux 4.1: cesium carbonate or Cs2O3 / N,N-dimethyl-formamide / 2 h / 130 °C 5.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6.1: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 7.2: 0.5 h / 20 °C 8.1: iron; acetic acid / 1 h / 60 °C 9.1: toluene; chloroform / 2 h / 80 °C 10.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4: caesium carbonate / N,N-dimethyl-formamide / 2 h / 130 °C 5: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7: acetic acid; iron / 1 h / 60 °C | ||
Multi-step reaction with 7 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: acetic acid; hydrogen bromide / Sealed tube; Reflux 4: cesium carbonate or Cs2O3 / N,N-dimethyl-formamide / 2 h / 130 °C 5: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7: iron; acetic acid / 1 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4: caesium carbonate / N,N-dimethyl-formamide / 2 h / 130 °C 5: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7: acetic acid; iron / 1 h / 60 °C 8: toluene; chloroform / 2 h / 80 °C | ||
Multi-step reaction with 8 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: acetic acid; hydrogen bromide / Sealed tube; Reflux 4: cesium carbonate or Cs2O3 / N,N-dimethyl-formamide / 2 h / 130 °C 5: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7: iron; acetic acid / 1 h / 60 °C 8: toluene; chloroform / 2 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4: caesium carbonate / N,N-dimethyl-formamide / 2 h / 130 °C 5: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7: acetic acid; iron / 1 h / 60 °C 8: toluene; chloroform / 2 h / 80 °C 9: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C | ||
Multi-step reaction with 9 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: acetic acid; hydrogen bromide / Sealed tube; Reflux 4: cesium carbonate or Cs2O3 / N,N-dimethyl-formamide / 2 h / 130 °C 5: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 20 °C 6: diphenyl phosphoryl azide; triethylamine / toluene / 3.5 h / 20 °C / Reflux 7: iron; acetic acid / 1 h / 60 °C 8: toluene; chloroform / 2 h / 80 °C 9: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: hydrogen bromide / acetic acid / 100 °C / Sealed tube | ||
Multi-step reaction with 3 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: acetic acid; hydrogen bromide / Sealed tube; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C | ||
Multi-step reaction with 4 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: acetic acid; hydrogen bromide / Sealed tube; Reflux 4: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C 5: acetic acid; iron / 1 h / 60 °C | ||
Multi-step reaction with 5 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: acetic acid; hydrogen bromide / Sealed tube; Reflux 4: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C 5: iron; acetic acid / 1 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: hydrogen bromide / acetic acid / 100 °C / Sealed tube 4: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C 5: acetic acid; iron / 1 h / 60 °C 6: toluene / 2 h / 80 °C | ||
Multi-step reaction with 6 steps 1: toluene / Reflux 2: triethylamine / ethanol / 0.5 h / 105 °C 3: acetic acid; hydrogen bromide / Sealed tube; Reflux 4: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C 5: iron; acetic acid / 1 h / 60 °C 6: toluene / 2 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene Reflux; | 7 Synthesis of compound 13 A mixture of compound 12 (1.5 g, 8.37 mmol) and compound 4 (2-bromine-4'-nitrobenzene ketone) (2.04 g, 8.37 mmol) in 5 ml of toluene was refluxed overnight. Filtration of resulted precipitate to afford the crude compound 13 (2.7 g, yield 76%) as a yellow solid, used in the next step without further purification. | |
In toluene Reflux; | 7.13 Synthesis of Compound 13 [0225] A mixture of compound 12 (1.5 g, 8.37 mmol) andcompound 4 (2-bromine-4'-nitrobenzene ketone) (2.04 g,8.37 mmol) in 5 ml of toluene was refluxed overnight. Filtrationof resulted precipitate to afford the crude compound 13(2.7 g, yield 76%) as a yellow solid, used in the next stepwithout further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -65 - -50 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice 3: hydrogenchloride; iron; acetic acid / ethanol 4: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -65 - -50 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -65 - -50 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice 3: hydrogenchloride; iron; acetic acid / ethanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -65 - -50 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice 3: hydrogenchloride; iron; acetic acid / ethanol; water 4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice | ||
Multi-step reaction with 2 steps 1: lithium diisopropyl amide / tetrahydrofuran 2: lithium hexamethyldisilazane / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.17 h / -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: hydrogenchloride; iron; acetic acid / ethanol; water / 20 °C 4.1: sodium methylate / methanol / 3 h / Reflux 4.2: 1 h / 0 °C / Reflux 5.1: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 5 steps 1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -65 - -50 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice 3: hydrogenchloride; iron; acetic acid / ethanol; water 4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice 5: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 5 steps 1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.33 h / -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: iron; hydrogenchloride / ethanol; water / 4 h / 70 °C 4.1: sodium methylate / methanol / 2 h / Reflux; Enzymatic reaction 4.2: 2.33 h / 0 °C / Reflux 5.1: boron tribromide / dichloromethane / 19 h / -10 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.17 h / -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: hydrogenchloride; iron; acetic acid / ethanol; water / 20 °C 4.1: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere 5.1: dmap / N,N-dimethyl-formamide / 20 °C | ||
Multi-step reaction with 5 steps 1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -65 - -50 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice 3: hydrogenchloride; iron; acetic acid / ethanol; water 4: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere 5: 1H-imidazole / dimethyl sulfoxide / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: 6-methoxy-2-methylbenzothiazole With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: diethyl chlorophosphate In tetrahydrofuran; hexane at -78 - 20℃; for 1.33h; Inert atmosphere; | 1 Diethyl ( ( 6-methoxybenzo[d]thiazol-2-yl)methyl)phosphonate To a stirred solution of n-BuLi (2.5 M in hexanes, 25 mL, 62.5 mmol) in anhydrous THF (25 mL) was added diisopropylamine (6.55 g, 65.5 mmol) at -78°C under N2 atmosphere. The mixture stirred at this temperature for 50 minutes. A solution of 6-methoxy-2-methylbenzothiazole (4.7 g, 26.1 mmol) in anhydrous THF (40 mL) was added dropwise to the mixture and the resulting reddish solution stirred for 30 minutes at -78°C. A solution of diethylchlorophosphate (5.16 g, 30.0 mmol) in anhydrous THF (20 mL) was then added dropwise and the reaction mixture stirred for 10 minutes at -78°C. The reaction mixture was then allowed to warm up to room temperature (rt) and stirred at rt for 1 hour. The reaction was quenched with aqueous 1 N NH4CI (100 mL), and extracted with CHCl3. The combined organic layers were washed with aqueous 2% Na2CO3, brine and dried over anhydrous Na2SO4, filtered and concentrated in a vacuum. The crude product was purified by column chromatography (0-100% EtOAc in hexanes) to afford the title compound as a red oil (7.0 g, 77%).1H NMR (CHCl3) δ 7.88 (d, J = 8.8 Hz, 1H), 7.30 (d, J = 2.4 Hz, 1H), 7.07 (dd, J = 2.4, 8.8 Hz, 1H), 4.15 (quint, J = 7.2 Hz, 4H), 3.87 (s, 3H), 3.69 (d, J = 21.6 Hz, 2H), 1.31 (t, J = 7.2 Hz, 6H). |
70% | With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78 - 20℃; for 6h; Inert atmosphere; | 30 Example 30: Diethyl ((6-methoxybenzo[d]thiazol-2-yl)methyl)phosphonate (32) n-butyllithium (2.42 mL, 6.06 mmol), diisopropylamine (0.868 mL, 6.06 mmol) and 6-methoxy-2-methylbenzothiazole (0.415 mL, 2.71 mmol) were added to anhydrous tetrahydrofuran (25 mL). ) Was stirred for 30 minutes at -78 under nitrogen conditions. Diethyl phosphorochloridate (0.443 mL, 2.98 mmol) was added to the resulting red reaction mixture, followed by stirring at room temperature for 6 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture to complete the reaction. The reaction mixture was extracted with dichloromethane, sodium sulfate was added, dried, and then distilled under reduced pressure to remove the solvent. The residue was purified by column chromatography (elution solvent: ethyl acetate/n-hexane=1/1), and compound 32 as an orange oil (diethyl ((6-methoxybenzo[d]thiazol-2-yl)) Methyl)phosphonate; 594.4 mg, 70%) was synthesized. |
67% | Stage #1: 6-methoxy-2-methylbenzothiazole With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: diethyl chlorophosphate In tetrahydrofuran; hexane at -78 - 20℃; for 1.16667h; Inert atmosphere; | (c) Diethyl ((6-methoxybenzo[d]thiazol-2-yl)methyl)phosphonate (2) To a stirred solution of n-BuLi (2.5M in hexanes, 25mL, 62.5mmol)) in anhydrous THF (25mL) was added diisopropylamine (8.76mL, 62.5mmol) at -78°C under N2 atmosphere. The mixture was stirred at this temperature for 30min. To this LDA mixture, a solution of 6-methoxy-2-methylbenzothiazole (5.00g, 27.9mmol) in anhydrous THF (40mL) was added dropwise and the resulting reddish solution was stirred 30min at -78°C. Then, a diethylchlorophosphate (4.44mL, 30.7mmol) solution in anhydrous THF (20mL) was added dropwise. After the reaction mixture was stirred 10min at -78°C, it was allowed to warm up to rt and stirred at rt for 1h. The reaction was quenched with aqueous 1N NH4Cl (100mL), and the mixture was extracted with CHCl3. The combined organic layer was washed with aqueous 2% Na2CO3, brine and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography with CH2Cl2/MeOH (250:5) as eluent to afford compound 2 as an orange oil (5.91g, 67%). 1H NMR (CDCl3): δ 7.79 (d, J=9.0Hz, 1H), 7.22 (d, J=2.5Hz, 1H), 6.98 (dd, J=2.5, 9.0Hz, 1H), 4.06 (quin, J=2.0Hz, 4H), 3.78 (s, 3H), 3.62 (d, J=21.5Hz, 2H), 1.24 (t, J=2.0Hz, 6H). |
67% | Stage #1: 6-methoxy-2-methylbenzothiazole With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: diethyl chlorophosphate In tetrahydrofuran; hexane at -78 - 20℃; for 1.16667h; Inert atmosphere; | S2 S2: Preparation of compound 1-4 diethyl ((6-methoxybenzo[d]thiazol-2-yl)methyl)phosphonate Under nitrogen protection at -78°C, diisopropylamine (8.76mL, 62.5mmol) was added dropwise to n-butyllithium (2.5M, n-hexane, 25mL, 62.5mmol) in anhydrous THF (25mL)In the solution, stir for 30 min, add dropwise a solution of 6-methoxy-2-methylbenzo[d]thiazole (5.00 g, 27.9 mmol) in anhydrous THF (40 mL), stir at -78°C for 30 min,Then, a solution of diethyl chlorophosphate (4.44ml, 30.7mmol) in anhydrous THF (20mL) was added dropwise, and the reaction solution was stirred at -78°C for 10 min.Warm up to room temperature, stir for 1 h, quench with 1N ammonium chloride aqueous solution (100 mL), extract with DCM, wash the organic layer with 2% sodium carbonate aqueous solution,Wash with brine, dry with anhydrous sodium sulfate, filter,Concentrate under reduced pressure and perform silica gel column chromatography (dichloromethane/methanol=50:1) to obtain 5.91 g of orange oily compound I-4 diethyl ((6-methoxybenzo[d]thiazol-2-yl)methyl)phosphonate, the yield is 67%; |
6.30 g | With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -65 - -50℃; Inert atmosphere; | 30.1 (Step 1: Synthesis of Compound (6)) (Step 1: Synthesis of Compound (6)) Under an argon atmosphere, after a tetrahydrofuran solution (75 mL) of diisopropylamine (5.06 g, 50.0 mmol) was cooled down to -50°C, n-butyllithium (1.6 M hexane solution, 31.2 mL, 50.0 mmol) was added dropwise. The reaction liquid was cooled down to -65°C, and a tetrahydrofuran solution (25 mL) of 6-methoxy-2-methylbenzothiazole (5)(4.48 g, 25.0 mmol) was added dropwise. Diethyl chlorophosphate (4.31 g, 25.0 mmol) was added dropwise to the reaction liquid. After the disappearance of the raw material, the reaction liquid was added in 100 mL of a 1M hydrogen chloride solution, and the organic layer was extracted with chloroform. The organic layer was dried with anhydrous sodium sulphate, and the solvent was distillated under reduced pressure. By refining the residue by column chromatography (developing solvent: chloroform), 6.30 g of the title compound (6) was obtained. |
Stage #1: 6-methoxy-2-methylbenzothiazole With lithium diisopropyl amide In tetrahydrofuran Stage #2: diethyl chlorophosphate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In water; dimethyl sulfoxide at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / dimethyl sulfoxide; water / 12 h / 20 °C 2: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide / dimethyl sulfoxide; water / 12 h / 20 °C 2: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere 3: caesium carbonate / N,N-dimethyl-formamide / 5 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With iodine; toluene-4-sulfonic acid In dimethyl sulfoxide at 130℃; for 16h; Schlenk technique; | |
With selenium(IV) oxide | ||
With selenium(IV) oxide In 1,4-dioxane at 110℃; for 12h; | 6.1. Benzo[d]thiazole-2-carbaldehyde (14a) General procedure: 2-methylbenzo[d]thiazole (13a, 745mg, 5mmol) was refluxed with selenium dioxide (2775mg, 25mmol) in dioxane for 12h. After completion of the reaction the black solid of Selenium was filtered off on celite and the dioxane was removed under reduced pressure. Water was added to the reaction mixture and the compound was extracted using ethyl acetate. The compound was further purified using column chromatography on silica gel 60-120 mesh to afford the pure solid in moderate yield (52%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.17 h / -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.33 h / -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.17 h / -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.17 h / -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: hydrogenchloride; iron; acetic acid / ethanol; water / 20 °C | ||
Multi-step reaction with 3 steps 1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.33 h / -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: iron; hydrogenchloride / ethanol; water / 4 h / 70 °C | ||
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.17 h / -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice 3.1: acetic acid; iron; hydrogenchloride / ethanol / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.17 h / -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: hydrogenchloride; iron; acetic acid / ethanol; water / 20 °C 4.1: sodium methylate / methanol / 3 h / Reflux 4.2: 1 h / 0 °C / Reflux | ||
Multi-step reaction with 4 steps 1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.33 h / -78 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: iron; hydrogenchloride / ethanol; water / 4 h / 70 °C 4.1: sodium methylate / methanol / 2 h / Reflux; Enzymatic reaction 4.2: 2.33 h / 0 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35.3% | With acetic acid at 145℃; for 0.333333h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.4% | at 100℃; for 24h; | 3 Production of Compound 3 Ethyl iodide (iodoethane) (2.00 mL, 24.6 mmol, commercial product) solution of 6-methoxy-2-methylbenzothiazole (201 mg, 1.12 mmol, commercial product) was heated and refluxed (oil bath temperature 100° C.) for 24 hours. After the solution was cooled at room temperature, a colorless solid substance formed was collected by filtration, washed with ethyl acetate, and dried under a reduced pressure, whereby 3-ethyl-6-methoxy-2-methylbenzothiazolium iodide (257 mg, 0.766 mmol, 68.4%) was obtained in a colorless solid state. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water-d2; benzoic acid at 120℃; for 8h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With iodine; oxygen; dimethyl sulfoxide; salicylic acid at 100℃; for 16h; Schlenk technique; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ytterbium(III) triflate In 1,2-dichloro-ethane at 50℃; Schlenk technique; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With copper(II) bis(trifluoromethanesulfonate); 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] In dichloromethane at 0℃; for 65h; Schlenk technique; Inert atmosphere; Molecular sieve; Sealed tube; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene for 12h; Reflux; Inert atmosphere; | 3.5.1 (1) 2-Methyl-5-methoxybenzothiazole (III4e) (1 mol), bromoethanol (3 mol) was placed together in 20 mL of dry toluene, and heated under reflux for 12 hours under nitrogen atmosphere.It was cooled to room temperature, washed with anhydrous diethyl ether and recrystallized from acetone to give a white-yellow solid quaternary ammonium salt (III6d) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium iodide In 1,2-dichloro-benzene for 24h; Reflux; Inert atmosphere; | 8.5.1 (1) 2-methyl-5-benzyloxy-benzothiazole (III8e) (1 mol),3-furanylmethyl chloride (2 mol) was placed together in 20 mL of dry o-dichlorobenzene solvent, potassium iodide was added as a catalyst, and heated under reflux for 24 hours under nitrogen atmosphere.It was cooled to room temperature, washed with anhydrous diethyl ether and recrystallized from acetone to give a white-yellow solid quaternary ammonium salt (III9d) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium iodide In 1,2-dichloro-benzene for 36h; Reflux; Inert atmosphere; | 9.5.1 (1) 2-methyl-5-methoxybenzothiazole (II8e) (1 mol), p-hexylbenzyl bromide (2 mol) in 20 mL of dry o-dichlorobenzene solvent, Potassium iodide was added as a catalyst, and heated under reflux for 36 hours under nitrogen atmosphere.It was cooled to room temperature, washed with anhydrous diethyl ether and recrystallized from acetone to give a dark gray solid quaternary ammonium salt (II9d) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With di-tert-butyl peroxide In fluorobenzene at 130℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-tert-butyl peroxide In fluorobenzene at 130℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 40% 2: 26% | Stage #1: 6-methoxy-2-methylbenzothiazole With sulfuric acid; hydroxylamine hydrochloride In acetonitrile at 25℃; for 0.166667h; Stage #2: With hydrogenchloride; titanium(III) chloride In water; acetonitrile at 25℃; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Stage #1: 6-methoxy-2-methylbenzothiazole With lithium diisopropyl amide In tetrahydrofuran at -70℃; for 0.5h; Stage #2: Dimethyl chlorophosphate In tetrahydrofuran at -70 - 25℃; for 0.5h; | 1 Step 1 To a solution of lithium diisopropylamide (2 M, 16.74 mL, 3 eq) was added 6-methoxy-2- methyl-l,3-benzothiazole (2 g, 11.16 mmol, 1 eq) in tetrahydrofuran (20 mL) at -70 °C. Then the mixture was stirred at -70 °C for 30 min. Dimethyl phosphorochloridate (1.61 g, 11.16 mmol, 1 eq) was added into the mixture at -70 °C, and the mixture was stirred at -70 °C for 10 min and at 25 °C for 1 hour 20 min. The mixture was quenched with saturated solution of ammonium chloride (20 mL), extracted with ethyl acetate (20 mL x 3), washed with brine (30 mL), dried over sodium sulfate, filtered and then concentrated. The residue was purified by prep-TLC (petroleum ether: ethyl acetate=3: 1). 2-(Dimethoxyphosphorylmethyl)-6- methoxy-l,3-benzothiazole (1.7 g, 5.92 mmol, 53% yield) was obtained as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: dimethyl sulfoxide 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.08 h / 20 °C 2.2: 0.17 h 2.3: 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In dimethyl sulfoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium methoxide / dimethyl sulfoxide; methanol / 20 °C 2: aq. phosphate buffer; dimethyl sulfoxide / 20 °C / pH Ca. 7.4 / Irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With sodium methoxide In methanol; dimethyl sulfoxide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83 % ee | Stage #1: 6-methoxy-2-methylbenzo[d]thiazole With 5-((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-5H-dibenzo[b,f]azepine; di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium; 2,2,6,6-tetramethylpiperidinylzinc bromide lithium bromide complex In 1,4-dioxane at 25℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: Carbonic acid 1-(2-fluoro-phenyl)-allyl ester methyl ester In 1,4-dioxane at 25℃; Inert atmosphere; Schlenk technique; Overall yield = 60 percent; Overall yield = 35.6 mg; enantioselective reaction; |
Tags: 2941-72-2 synthesis path| 2941-72-2 SDS| 2941-72-2 COA| 2941-72-2 purity| 2941-72-2 application| 2941-72-2 NMR| 2941-72-2 COA| 2941-72-2 structure
[ 943-03-3 ]
6-Methoxybenzo[d]thiazole-2-carbonitrile
Similarity: 0.93
[ 101078-51-7 ]
6-Methoxy-2-(p-tolyl)benzo[d]thiazole
Similarity: 0.85
[ 6294-52-6 ]
5,6-Dimethoxybenzo[d]thiazol-2-amine
Similarity: 0.80
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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