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CAS No. : | 24964-76-9 | MDL No. : | MFCD00059382 |
Formula : | C10H22O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KOPMZTKUZCNGFY-UHFFFAOYSA-N |
M.W : | 190.28 | Pubchem ID : | 371779 |
Synonyms : |
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Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P305+P351+P338 | UN#: | 1993 |
Hazard Statements: | H225-H315-H319 | Packing Group: | Ⅲ |
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 |
---|---|---|
94.4% | With methanesulfonic acid In N,N-dimethyl-formamide at 70℃; for 9 h; | 5 g of compound 12 was added to 30 mL of DMF, 4.1 g of triethyl orthobutyrate and 0.5 g of methanesulfonic acid were added, and the mixture was heated with stirringTo 70 , the reaction 9h. The reaction was monitored by HPLC to control the remaining amount of raw materials to be 0.5percent or less of the initial amount. Ice bath cooling crystallization 2h, vacuum suction filtration. The wet product was dried at 80 ° C to give 6.2 g of white solid compound 2 as a white solid, yield 94.4percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In chloroform; | EXAMPLE 5 4-Chloro-1-n-propyl-[1,2,4]triazolo[4,3-a]quinoxaline 2-Chloro-3-hydrazinoquinoxaline (3.0 g., 0.015 mole), the product of Example 1, was stirred with <strong>[24964-76-9]triethyl orthobutyrate</strong> (27 ml.) at 100 C. for 2 hours. The mixture was cooled to room temperature, and the precipitate was collected by filtration and washed with cyclohexane. The crude solid was taken up in chloroform and filtered to remove insoluble material. The chloroform solution was concentrated in vacuo to give a solid which was recrystallized from chloroform to give 1.96 g. (53% yield) of 4-chloro-1-n-propyl-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 173-175 C. Mass spectrum: m/e, 246 (P). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In N,N-dimethyl-formamide; at 100℃; for 12h; | General procedure: The magnetically stirred mixture of 4a (0.41 g, 2.5 mmol) and triethyl orthoformate (0.3 g, 5 mmol, 2 equiv) in DMF (2.5 mL) was treated at 100 C (oil bath) for 12 h. The crude reaction mixture was poured into crushed ice (10 g) and the precipitated solid was filtered to obtain 6a as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; magnesium sulfate; at 140℃; for 4 - 6h;Product distribution / selectivity; | Example 6 ethyl-2-(1-ethoxyethylidene)-acetoacetate To ethyl-diacetoacetate (510 mg, 2.96 mmol) were added <strong>[24964-76-9]triethyl orthobutyrate</strong> (845 mg, 4.39 mmol), magnesium sulfate (200 mg) and sulfuric acid (5 μl), and the mixture was heated at 140C for 6 hr. MTBE was added, and the precipitate was filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give an oil containing ethyl-2-(1-ethoxyethylidene)-acetoacetate (449 mg, 2.24 mmol). Example 11: ethyl 4,6-methyl-2-methylthiopyrimidine-5-carboxylate ; To ethyl diacetoacetate (510 mg, 2.96 mmol) were added trimethyl orthobutyrate (845 mg, 4.39 mmol), magnesium sulfate (200 mg) and sulfuric acid (5 µl), and the mixture was stirred at 140C for 4 hr in an oil bath. The reaction mixture was concentrated under reduced pressure. The residue was added to a suspension of methylisothiourea sulfate (412 mg, 1.48 mmol) and sodium carbonate (320 mg, 3.01 mmol) in ethyl acetate, and the mixture was stirred at 80C overnight. After cooling, the mixture was washed successively with water and saturated brine, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (365 mg, 1.61 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | at 140℃; for 0.5h; | A mixture of triethylorthobutyrate (6.9 [ML,] 31.9 mmole) and malonitrile (2.00 [ML,] 31.8 mmole) was heated to 140C for 30 minutes. During the course of the reaction ethanol was removed by distillation. Cooling the reaction mixture provided the product as a yellow oil (5.02 g, 96%). ['H] NMR [(CDCI3)] : [8] 4.42 (q, 2H), 2.60 (t, 2H), 1.67 (m, 2H), 1.44 (t, 3H), 1.04 (t, 3H) ppm. |
With acetic acid; In ethanol; at 95℃; | 1,1, 1-triethoxybutane (69 g, 362.62 mmol) was added to a solution of malononitrile (20 g, 302.75 mmol) in AcOH (70 mL)/ethanol (70 mL), and the reaction was stirred overnight at 95C. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether = 1 :2). The resulting mixture was concentrated in vacuo to afford 2-(l-ethoxybutylidene)propanedinitrile as a red oil (45 g, crude). LC-MS: (ES, m/z): [M+H]+ 165 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; | Part A: 3-Methoxymethyl-5-propyl-4-[(2'-carbomethoxy-biphenyl-4-yl)methyl]-1.2.4-triazole This compound was prepared according to the method described for Example 67, Part B. From triethyl orthobutyrate (3.1 g, 16.2 mmol) methoxyacetyl hydrazide (1.7 g, 16.2 mmol) DBU (1.8 ml, 11.9 mmol) and methyl 4'-aminomethylbiphenyl-2-carboxylate hydrochloride (3.0 g, 10.8 mmol) in refluxing xylenes (50 ml) was obtained 2.3 g (56percent) of the title compound as a colorless oil following flash chromatography. NMR (200 MHz;CDCl3, TMS) delta: 7.88-7.04 (m,8H), 5.25 (s,2H), 4.56 (s,2H), 3.65 (s,3H), 3.34 (s,3H), 2.66 (t,J=7 Hz,2H), 1.78 (m,2H), 0.98 (t,J=7 Hz,3H). | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene; | Part A 3-Methoxymethyl-5-propyl-4-[(2'-carbomethoxybiphenyl-4-yl)methyl]-1,2,4-triazole This compound was prepared according to the method described for Example 67, Part B. From triethyl orthobutyrate (3.1 g, 16.2 mmol) methoxyacetyl hydrazide (1.7 g, 16.2 mmol) DBU (1.8 ml, 11.9 mmol) and methyl 4'-aminomethylbiphenyl-2-carboxylate hydrochloride (3.0 g, 10.8 mmol) in refluxing xylenes (50 ml) was obtained 2.3 g (56percent) of the title compound as a colorless oil following flash chromatography. NMR (200 MHz;CDCl3,TMS)delta: 7.88-7.04(m,8H), 5.25(s,2H), 4.56(s,2H), 3.65(s,3H), 3.34(s,3H), 2.66(t,J=7 Hz,2H), 1.78(m,2H), 0.98(t,J=7 Hz,3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; | Part A 3-Methoxymethyl-5-propyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-1,2,4-triazole This compound was prepared according to the methods described for Example 67, Part B. From triethyl orthobutyrate (2.3 g, 12.3 mmol) methoxyacetyl hydrazide (1.4 g, 12.3 mmol), DBU (1.4 ml, 8.9 mmol) and 4'-aminomethylbiphenyl-2-nitrile (2.0 g, 8.2 mmol) in refluxing xylenes (50 ml) was obtained 1.6 g (57percent) of the title compound, as a viscous oil which slowly crystallized upon standing at room temperature. NMR (200 MHz;CDCl3,TMS)delta: 7.80-7.12(m,8H), 5.28(s,2H), 4.56(s,2H), 3.34(s,3H), 2.65(t,J=7 Hz,2H), 1.78(m,2H), 0.99(t,J=7 Hz,3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine hydrochloride; In acetonitrile; for 0.666667h; | Part A Triethyl orthobutyrate (2.2 mL, 14 mmol) was added to a stirred solution of N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine (3.6 g, 12 mmol) in acetonitrile (60 mL). Pyridine hydrochloride (0.3 g) was added and the reaction mixture was heated to reflux with the volatiles being collected in a Dean Stark trap. After 40 minutes analysis by TLC indicated that the starting material was consumed. The reaction mixture was concentrated under reduced pressure to provide 3.7 g of 1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-2-propyl-1H-imidazo[4,5-c]quinoline as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | a): The following reagents were heated in toluene (30 ml) in a stainless steel autoclave (purged with nitrogen) in an oil bath at 195-200 C for 24 hours: l-cyclohexyl-2- methylprop-2-en-l-ol (31.47 g; 201 mmol); <strong>[24964-76-9]triethyl orthobutyrate</strong> (44 g; 208 mmol); 2-ethylhexanoic acid (1.5 g; 10.5 mmol). The reaction was cooled to room temperature, diluted with diethyl ether, shaken for 5 minutes with 1 % aq. HC1. The phases were separated. The aqueous phase was re-extracted with diethyl ether. Each organic phase was washed with aqueous sat. NaHCC>3 and brine. Combined extracts were dried over sodium sulfate. The product was sufficiently pure and directly used as such in the next step. The above obtained crude ester was added drop-wise (over 2 hours) to a slurry of lithium aluminum hydride (11 g; 275 mmol) in THF (800 ml), under nitrogen and ice-water cooling. The cooling bath was removed and the reaction stirred until room temperature was reached (2 hours). The reaction was cooled into an ice-water bath, and water (11 ml); 5 % aqueous NaOH (33 ml) and water (11 ml) were cautiously added. The reaction was warmed up to room temperature and stirred until a white slurry was obtained (30 min). Solid, anhydrous sodium sulfate (50 g) was added and the mixture was stirred for 15 minutes. The solid was filtered off, rinsed with diethyl ether. The filtrate was concentrated on the rotavapor. The ester thus obtained was purified by bulb-to-bulb distillation (90 C/0.004 mbar) and recovered with 95 % yield for the 2 steps. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
832 mg | General procedure: To a solution of 1,2-diamine component 3 (3.0 mmol) in toluene (10 mL) was added the corresponding orthoester (7.5 mmol). The reaction mixture was stirred at 80 C for 3-18 h, and the reaction mixture was concentrated in vacuo. In the case of 4d-e syntheses, the residue was once dissolved in MeOH/THF (1:1, 2 mL) and 1 M NaOH (3.0 mmol) was added at 0 C. The stirring was kept for 2 h at room temperature. The reaction mixture was concentrated under vacuum. The residue was diluted with CHCl3. The organic layer was washed with 10 % citric acid and sat. NaCl, and dried over Na2SO4. The organic solvent was concentrated under reduced pressure to afford the crude product, followed by column chromatography over SiO2 gel using CHCl3/MeOH as eluent solvent systems to obtain pure product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With acetic acid; In ethanol;Reflux; Inert atmosphere; | General procedure: The orthoester (1.5 equiv) was added to a mixture of the 2-aminobenzamide (1.0 equiv) in absoluteethanol (3 mL). Glacial acetic acid (2 equiv) was added and the reaction was heated at reflux for 12-24 h.The reaction mixture was cooled and concentrated under vacuum. If the crude product was pure by1H-NMR, it was triturated with 5% ether in pentane. If it was not pure, it was recrystallized fromethanol. In some cases, it was necessary to remove excess orthoester under high vacuum at 50 C prior to purification. The following compounds were prepared: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
165 g | With toluene-4-sulfonic acid; at 78℃; for 7h; | Example 1 (0039) Process for Preparing 1,1,1 Triethoxy Butane (0040) 70 gms of crotonaldehyde, 920 gms of ethyl alcohol was charged in to a round bottom flask, which was attached to a reflux condensor. 10 gms of paratoulene sulphonic acid was added to the round bottom flask and the contents were heated at a temperature of 78 C. for 7 hours. After heating, the reaction mass was cooled and was neutralized by adding 4 gms of sodium carbonate at room temperature to obtain 1,1,1 triethoxy butane and polymer. The reaction mass was distilled at atmospheric pressure to recover ethyl alcohol and remove low boiling impurities. The recovered ethyl alcohol was recycled back to the round bottom flask containing crotonaldehyde, ethyl alcohol and para toluene sulphonic acid. The remaining product obtained was 165 gms of 1,1,1 triethoxy butane. The flash point of 1,1,1 triethoxy butane was 64 C. (0041) 1,1,1 triethoxy butane having high flash point of 64 C. was tested under standard conditions for its frothing properties. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.4% | With methanesulfonic acid; In N,N-dimethyl-formamide; at 70℃; for 9h; | 5 g of compound 12 was added to 30 mL of DMF, 4.1 g of triethyl orthobutyrate and 0.5 g of methanesulfonic acid were added, and the mixture was heated with stirringTo 70 , the reaction 9h. The reaction was monitored by HPLC to control the remaining amount of raw materials to be 0.5% or less of the initial amount. Ice bath cooling crystallization 2h, vacuum suction filtration. The wet product was dried at 80 C to give 6.2 g of white solid compound 2 as a white solid, yield 94.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | at 120℃; for 1h; | To a solution of malononitrile (25 g, 378 mmol) and <strong>[24964-76-9]1,1,1-triethoxybutane</strong> (40 g, 210 mmol) in pyridine (16 mL) stirred in air at 20 C. The reaction mixture was stirred at 120 C for 1 hour. The mixture was concentrated, EtOAc was added, and the solid was filtered to obtain pyridin-1-ium (E)-1,1-dicyano-2-(cyano(isocyano)methylene)butan-1-ide (10 g, 19%) which was used in the next step without further purification. 1H NMR (400 MHz, DMSO) δ ppm 8.93 (d, J = 5.1 Hz, 2H), 8.62- 8.54 (m, 1H), 8.06 (dd, J = 7.7, 6.6 Hz, 1H), 2.33 (q, J = 7.5 Hz, 2H), 1.09 (t, J = 7.6 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
By the reaction of anthranilamide and triethyl butyrate at 130C overnight, an intermediate propyl quinazolinone is obtained through a condensation reaction,Then bromine is used as a bromine reagent and glacial acetic acid is used as a solvent.Sodium acetate was used as a base catalyzed reaction and reacted at 60C for 4 hours.Nucleophilic substitution reaction with bromineBromo intermediate 2-bromopropyl quinazolinone was obtained.The 2-bromopropylquinazolone intermediate obtained above was refluxed with 3.5 equivalents of p-fluorophenylhydrazine hydrochloride in ethanol.The phenylhydrazone intermediate F-IQ3 was prepared by nucleophilic substitution and elimination reactions, intermediate F-IQ4 was prepared by a classical Fischer indole synthesis method.Intermediate F-IQ4 was chlorinated with phosphorous oxychloride to give intermediate F-IQ7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
By anthranilamide and triethyl butyrate at 130 C overnight,The intermediate propyl quinazolinone is obtained by a condensation reaction,Then bromine is used as a bromine reagent and glacial acetic acid is used as a solvent.Sodium acetate was used as a base catalyzed reaction and reacted at 60C for 4 hours.Nucleophilic substitution reaction with bromineBromo intermediate 2-bromopropyl quinazolinone was obtained.The intermediate 2-bromopropylquinazolone obtained above and 3.5 equivalents of phenylhydrazine hydrochloride were refluxed in ethanol.The phenylhydrazone intermediate 3Y-IQ3 was prepared by nucleophilic substitution and elimination reactions, intermediates 3Y-IQ4 were prepared by the classical Fischer indole synthesis method. Intermediates 3Y-IQ4 were reacted with phosphorus oxychloride to give intermediates 3Y-IQ7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With acetic acid; In ethanol; at 110℃; for 24h;Inert atmosphere; Sealed tube; | General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2-3 equiv) and absolute ethanol (2-3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 C for 12-72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5%ether in pentane. The following compounds were prepared: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With acetic acid; In ethanol; at 110℃; for 24h;Inert atmosphere; | General procedure: The orthoester (1.5 equiv) was added to a mixture of the <strong>[324763-51-1]3-amino-2,2-dimethylpropionamide</strong>(1.0 equiv) in anhydrous ethanol (3 mL). Glacial acetic acid (2 equiv) was added and the reactionwas heated at reflux for 24 h. The reaction mixture was cooled and concentrated under vacuum.The product was hygroscopic and was best crystallized by adding purified chloroform and allowing itto sit under nitrogen for 4-7 days. Filtration and drying yielded the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With acetic acid; In ethanol; at 110℃; for 24h;Inert atmosphere; Sealed tube; | General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2?3 equiv) and absolute ethanol (2?3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 °C for 12?72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5percentether in pentane. The following compounds were prepared: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With acetic acid; In ethanol; at 110℃; for 12h;Inert atmosphere; Sealed tube; | General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2-3 equiv) and absolute ethanol (2-3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 C for 12-72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5%ether in pentane. The following compounds were prepared: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With toluene-4-sulfonic acid; at 100℃; for 0.5h;Inert atmosphere; | 6'-Amino-8'-chloro-5'-hydroxy- H-spiro[cyclohexane-l,4'-quinazolin]-2'(3'H)-one (Intermediate 2, 30 mg, 0.11 mmol), 4-methylbenzenesulfonic acid (0.92 mg, 0.01 mmol) and <strong>[24964-76-9]1,1,1-triethoxybutane</strong> (0.30 mL, 1.4 mmol) were mixed together and stirred at 100C for 0.5 hour. The reaction mixture was cooled to room temperature and the crude material was diluted with MeOH (1 mL), filtered and purified by prep. HPLC (5-95% ACN-H2O). The desired fraction was lyophilized to afford the title compound as an off-white powder (7.4 mg, 21%). NMR (400 MHz, CDCb) δ 7.59 (s, 1H), 7.15 (br s, 1H), 5.60 (br s, 1H), 2.93 (t, / = 7.5 Hz, 2H), 2.30 (dt, / = 4.0, 13.5 Hz, 2H), 2.10 - 1.75 (m, 8H), 1.54 - 1.26 (m, 2H), 1.10 (t, / = 7.4 Hz, 3H). [M+H] = 334.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | General procedure: A solution of the newly afforded product (10.0 g, 40.3 mmol, 1.0eq) in triethylorthopropionate (16 mL, 80.6 mmol, 2.0 eq) was stirred at 130 C under N2 atmosphere. After TLC indicated the total conversion, removal of EtOH formed during the reaction and the excessive triethylorthopropionate under reduced pressure gave a viscous oil. Ph2O (30 mL) was then added and the resultant solution boiled at 250 C under N2 atmosphere for 4 h. Subsequently, it was totally cooled and kept at 10 C overnight. PE was added to the mixture, which was then stirred at room temperature. Following filtration, the precipitate was washed successively with PE and MeOH to afford 3-ethyl-2-phenyl-2H-benzo[e][1,2,4]thiadiazine1,1-dioxide 20 as a pale solid. Yield 94% (for two steps); 1H NMR(500 MHz, DMSO-d6): δ 7.95 (dd, 1.5 Hz, 8.0 Hz, 1H), 7.88-7.82 (m,1H), 7.67-7.63 (m, 1H), 7.62-7.56 (m, 4H), 7.53-7.48 (m, 2H), 2.33(q, 7.5 Hz, 2H), 1.11 (t, 7.5 Hz, 3H); ESI-MS: m/z 287 [MH]. Intermediates 21-31 were prepared in a procedure similar to that described for 20. For 21-29, the reaction mixture of the intramolecular cyclization was directly subjected to flash columnchromatography utilizing EA/PE (1:7) as the eluent to afford the product. As for 30 and 31, the intramolecular cyclization occurred when the reduced product of 19 was treated with corresponding orthoester. After removal of EtOH and the excessive orthoester, the residue was purified by flash column chromatography utilizing EA/PE (1:7) as the eluent to afford the product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | General procedure: A solution of the newly afforded product (10.0 g, 40.3 mmol, 1.0eq) in triethylorthopropionate (16 mL, 80.6 mmol, 2.0 eq) was stirred at 130 C under N2 atmosphere. After TLC indicated the total conversion, removal of EtOH formed during the reaction and the excessive triethylorthopropionate under reduced pressure gave a viscous oil. Ph2O (30 mL) was then added and the resultant solution boiled at 250 C under N2 atmosphere for 4 h. Subsequently, it was totally cooled and kept at 10 C overnight. PE was added to the mixture, which was then stirred at room temperature. Following filtration, the precipitate was washed successively with PE and MeOH to afford 3-ethyl-2-phenyl-2H-benzo[e][1,2,4]thiadiazine1,1-dioxide 20 as a pale solid. Yield 94% (for two steps); 1H NMR(500 MHz, DMSO-d6): δ 7.95 (dd, 1.5 Hz, 8.0 Hz, 1H), 7.88-7.82 (m,1H), 7.67-7.63 (m, 1H), 7.62-7.56 (m, 4H), 7.53-7.48 (m, 2H), 2.33(q, 7.5 Hz, 2H), 1.11 (t, 7.5 Hz, 3H); ESI-MS: m/z 287 [MH]. Intermediates 21-31 were prepared in a procedure similar to that described for 20. For 21-29, the reaction mixture of the intramolecular cyclization was directly subjected to flash columnchromatography utilizing EA/PE (1:7) as the eluent to afford the product. As for 30 and 31, the intramolecular cyclization occurred when the reduced product of 19 was treated with corresponding orthoester. After removal of EtOH and the excessive orthoester, the residue was purified by flash column chromatography utilizing EA/PE (1:7) as the eluent to afford the product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | General procedure: A solution of the newly afforded product (10.0 g, 40.3 mmol, 1.0eq) in triethylorthopropionate (16 mL, 80.6 mmol, 2.0 eq) was stirred at 130 C under N2 atmosphere. After TLC indicated the total conversion, removal of EtOH formed during the reaction and the excessive triethylorthopropionate under reduced pressure gave a viscous oil. Ph2O (30 mL) was then added and the resultant solution boiled at 250 C under N2 atmosphere for 4 h. Subsequently, it was totally cooled and kept at 10 C overnight. PE was added to the mixture, which was then stirred at room temperature. Following filtration, the precipitate was washed successively with PE and MeOH to afford 3-ethyl-2-phenyl-2H-benzo[e][1,2,4]thiadiazine1,1-dioxide 20 as a pale solid. Yield 94% (for two steps); 1H NMR(500 MHz, DMSO-d6): δ 7.95 (dd, 1.5 Hz, 8.0 Hz, 1H), 7.88-7.82 (m,1H), 7.67-7.63 (m, 1H), 7.62-7.56 (m, 4H), 7.53-7.48 (m, 2H), 2.33(q, 7.5 Hz, 2H), 1.11 (t, 7.5 Hz, 3H); ESI-MS: m/z 287 [MH]. Intermediates 21-31 were prepared in a procedure similar to that described for 20. For 21-29, the reaction mixture of the intramolecular cyclization was directly subjected to flash columnchromatography utilizing EA/PE (1:7) as the eluent to afford the product. As for 30 and 31, the intramolecular cyclization occurred when the reduced product of 19 was treated with corresponding orthoester. After removal of EtOH and the excessive orthoester, the residue was purified by flash column chromatography utilizing EA/PE (1:7) as the eluent to afford the product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | General procedure: A solution of the newly afforded product (10.0 g, 40.3 mmol, 1.0eq) in triethylorthopropionate (16 mL, 80.6 mmol, 2.0 eq) was stirred at 130 C under N2 atmosphere. After TLC indicated the total conversion, removal of EtOH formed during the reaction and the excessive triethylorthopropionate under reduced pressure gave a viscous oil. Ph2O (30 mL) was then added and the resultant solution boiled at 250 C under N2 atmosphere for 4 h. Subsequently, it was totally cooled and kept at 10 C overnight. PE was added to the mixture, which was then stirred at room temperature. Following filtration, the precipitate was washed successively with PE and MeOH to afford 3-ethyl-2-phenyl-2H-benzo[e][1,2,4]thiadiazine1,1-dioxide 20 as a pale solid. Yield 94% (for two steps); 1H NMR(500 MHz, DMSO-d6): δ 7.95 (dd, 1.5 Hz, 8.0 Hz, 1H), 7.88-7.82 (m,1H), 7.67-7.63 (m, 1H), 7.62-7.56 (m, 4H), 7.53-7.48 (m, 2H), 2.33(q, 7.5 Hz, 2H), 1.11 (t, 7.5 Hz, 3H); ESI-MS: m/z 287 [MH]. Intermediates 21-31 were prepared in a procedure similar to that described for 20. For 21-29, the reaction mixture of the intramolecular cyclization was directly subjected to flash columnchromatography utilizing EA/PE (1:7) as the eluent to afford the product. As for 30 and 31, the intramolecular cyclization occurred when the reduced product of 19 was treated with corresponding orthoester. After removal of EtOH and the excessive orthoester, the residue was purified by flash column chromatography utilizing EA/PE (1:7) as the eluent to afford the product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | General procedure: A solution of the newly afforded product (10.0 g, 40.3 mmol, 1.0eq) in triethylorthopropionate (16 mL, 80.6 mmol, 2.0 eq) was stirred at 130 C under N2 atmosphere. After TLC indicated the total conversion, removal of EtOH formed during the reaction and the excessive triethylorthopropionate under reduced pressure gave a viscous oil. Ph2O (30 mL) was then added and the resultant solution boiled at 250 C under N2 atmosphere for 4 h. Subsequently, it was totally cooled and kept at 10 C overnight. PE was added to the mixture, which was then stirred at room temperature. Following filtration, the precipitate was washed successively with PE and MeOH to afford 3-ethyl-2-phenyl-2H-benzo[e][1,2,4]thiadiazine1,1-dioxide 20 as a pale solid. Yield 94% (for two steps); 1H NMR(500 MHz, DMSO-d6): δ 7.95 (dd, 1.5 Hz, 8.0 Hz, 1H), 7.88-7.82 (m,1H), 7.67-7.63 (m, 1H), 7.62-7.56 (m, 4H), 7.53-7.48 (m, 2H), 2.33(q, 7.5 Hz, 2H), 1.11 (t, 7.5 Hz, 3H); ESI-MS: m/z 287 [MH]. Intermediates 21-31 were prepared in a procedure similar to that described for 20. For 21-29, the reaction mixture of the intramolecular cyclization was directly subjected to flash columnchromatography utilizing EA/PE (1:7) as the eluent to afford the product. As for 30 and 31, the intramolecular cyclization occurred when the reduced product of 19 was treated with corresponding orthoester. After removal of EtOH and the excessive orthoester, the residue was purified by flash column chromatography utilizing EA/PE (1:7) as the eluent to afford the product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | General procedure: A solution of the newly afforded product (10.0 g, 40.3 mmol, 1.0eq) in triethylorthopropionate (16 mL, 80.6 mmol, 2.0 eq) was stirred at 130 C under N2 atmosphere. After TLC indicated the total conversion, removal of EtOH formed during the reaction and the excessive triethylorthopropionate under reduced pressure gave a viscous oil. Ph2O (30 mL) was then added and the resultant solution boiled at 250 C under N2 atmosphere for 4 h. Subsequently, it was totally cooled and kept at 10 C overnight. PE was added to the mixture, which was then stirred at room temperature. Following filtration, the precipitate was washed successively with PE and MeOH to afford 3-ethyl-2-phenyl-2H-benzo[e][1,2,4]thiadiazine1,1-dioxide 20 as a pale solid. Yield 94% (for two steps); 1H NMR(500 MHz, DMSO-d6): δ 7.95 (dd, 1.5 Hz, 8.0 Hz, 1H), 7.88-7.82 (m,1H), 7.67-7.63 (m, 1H), 7.62-7.56 (m, 4H), 7.53-7.48 (m, 2H), 2.33(q, 7.5 Hz, 2H), 1.11 (t, 7.5 Hz, 3H); ESI-MS: m/z 287 [MH]. Intermediates 21-31 were prepared in a procedure similar to that described for 20. For 21-29, the reaction mixture of the intramolecular cyclization was directly subjected to flash columnchromatography utilizing EA/PE (1:7) as the eluent to afford the product. As for 30 and 31, the intramolecular cyclization occurred when the reduced product of 19 was treated with corresponding orthoester. After removal of EtOH and the excessive orthoester, the residue was purified by flash column chromatography utilizing EA/PE (1:7) as the eluent to afford the product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.09% | In ethanol; for 2h;Reflux; | Compound 2b (500 mg, 1.78 mmol) and the <strong>[24964-76-9]triethyl orthobutyrate</strong> (406 mg, 2.14 mmol) was dissolved in 20 mL of ethanol, and the reaction was stirred for 2 hours under reflux. The reaction was stopped, cooled to room temperature, and the reaction solution was concentrated under reduced pressure.The residue obtained was beaten with 5 mL of anhydrous diethyl ether for 0.5 hour.Filtration and drying of the filter cake gave the title compound 6a (580 mg, yield: 98.09%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.1% | In ethanol; for 3h;Reflux; | Compound 4g (500mg, 1.68mmol) was added to 15mL of ethanol.Triethyl orthobutyrate (638 mg, 3.35 mmol) was added, and the mixture was heated to reflux and stirred for 3 hours. The reaction was stopped, cooled to room temperature, filtered, and the filter cake was washed successively with ethyl alcohol (3mL) and diethyl ether (5mL×3), and the filter cake was collected.The filter cake was dried to give the title compound 9a (470mg, yield: 80.1%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59.07% | In ethanol; for 4h;Reflux; | The compound 10f (1 g, 3.16 mmol) and the (tri)ethyl butyrate (802 mg, 3.80 mmol) were dissolved in 50 mL of ethanol, and the reaction was stirred for 4 hours under reflux. The reaction was stopped, cooled to room temperature, and the reaction solution was concentrated under reduced pressure.The residue obtained was beaten with 50 mL of ethanol and n-hexane (V/V = 1/20) for 0.5 hour and filtered.The filter cake was dried to give the title compound 16a (688mg, yield: 59.07%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In N,N-dimethyl-formamide; at 100℃; for 12h; | General procedure: The magnetically stirred mixture of 4a (0.41 g, 2.5 mmol) and triethyl orthoformate (0.3 g, 5 mmol, 2 equiv) in DMF (2.5 mL) was treated at 100 C (oil bath) for 12 h. The crude reaction mixture was poured into crushed ice (10 g) and the precipitated solid was filtered to obtain 6a as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In N,N-dimethyl-formamide; at 100℃; for 12h; | General procedure: The magnetically stirred mixture of 4a (0.41 g, 2.5 mmol) and triethyl orthoformate (0.3 g, 5 mmol, 2 equiv) in DMF (2.5 mL) was treated at 100 C (oil bath) for 12 h. The crude reaction mixture was poured into crushed ice (10 g) and the precipitated solid was filtered to obtain 6a as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In N,N-dimethyl-formamide; at 100℃; for 12h; | General procedure: The magnetically stirred mixture of 4a (0.41 g, 2.5 mmol) and triethyl orthoformate (0.3 g, 5 mmol, 2 equiv) in DMF (2.5 mL) was treated at 100 C (oil bath) for 12 h. The crude reaction mixture was poured into crushed ice (10 g) and the precipitated solid was filtered to obtain 6a as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In N,N-dimethyl-formamide; at 100℃; for 12h; | General procedure: The magnetically stirred mixture of 4a (0.41 g, 2.5 mmol) and triethyl orthoformate (0.3 g, 5 mmol, 2 equiv) in DMF (2.5 mL) was treated at 100 C (oil bath) for 12 h. The crude reaction mixture was poured into crushed ice (10 g) and the precipitated solid was filtered to obtain 6a as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In N,N-dimethyl-formamide; at 100℃; for 12h; | General procedure: The magnetically stirred mixture of 4a (0.41 g, 2.5 mmol) and triethyl orthoformate (0.3 g, 5 mmol, 2 equiv) in DMF (2.5 mL) was treated at 100 C (oil bath) for 12 h. The crude reaction mixture was poured into crushed ice (10 g) and the precipitated solid was filtered to obtain 6a as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With acetic acid; at 100℃; for 24h;Inert atmosphere; | General procedure: The anthranilic acid (1.0 mmol) and the orthoester (4.5 mmol) were placed in a 15-mL Chemglassscrew-cap pressure tube (CG-1880-01, Vineland, NJ, USA). Glacial acetic acid (2.6 mmol) was added,N2 was introduced to the vessel and the cap was tightened. The vessel was heated at 100 C underneat conditions for 4-48 h, and then cooled to room temperature. Upon cooling, the crude productcrystallized from the reaction mixture and was purified by trituration from 5% ether in pentane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | at 100℃; for 0.75h;Microwave irradiation; Inert atmosphere; | General procedure: A solution of the anthranilic acid (1.0 mmol) in the orthoester (0.45 mL, 2.0-2.7 equivalents) wasprepared in a 5-mL microwave tube and stirred for 30 s prior to irradiation at the "high absorption"setting. The reaction was performed under N2 at 100 C (400 W) for 0.75-3 h. Upon cooling, the crudeproduct crystallized from the reaction mixture and was purified by trituration from 5% ether in pentane.The following compounds were prepared:2-Methyl-4H-benzo[d][1,3]oxazin-4-one (11a): 130 mg (81%, method 1) and 132 mg (82%, method 2) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | at 100℃; for 1.5h;Microwave irradiation; Inert atmosphere; | General procedure: A solution of the anthranilic acid (1.0 mmol) in the orthoester (0.45 mL, 2.0-2.7 equivalents) wasprepared in a 5-mL microwave tube and stirred for 30 s prior to irradiation at the "high absorption"setting. The reaction was performed under N2 at 100 C (400 W) for 0.75-3 h. Upon cooling, the crudeproduct crystallized from the reaction mixture and was purified by trituration from 5% ether in pentane.The following compounds were prepared:2-Methyl-4H-benzo[d][1,3]oxazin-4-one (11a): 130 mg (81%, method 1) and 132 mg (82%, method 2) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | at 100℃; for 0.75h;Microwave irradiation; Inert atmosphere; | General procedure: A solution of the anthranilic acid (1.0 mmol) in the orthoester (0.45 mL, 2.0-2.7 equivalents) wasprepared in a 5-mL microwave tube and stirred for 30 s prior to irradiation at the "high absorption"setting. The reaction was performed under N2 at 100 C (400 W) for 0.75-3 h. Upon cooling, the crudeproduct crystallized from the reaction mixture and was purified by trituration from 5% ether in pentane.The following compounds were prepared:2-Methyl-4H-benzo[d][1,3]oxazin-4-one (11a): 130 mg (81%, method 1) and 132 mg (82%, method 2) |
Tags: 24964-76-9 synthesis path| 24964-76-9 SDS| 24964-76-9 COA| 24964-76-9 purity| 24964-76-9 application| 24964-76-9 NMR| 24964-76-9 COA| 24964-76-9 structure
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H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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