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CAS No. : | 25185-95-9 | MDL No. : | MFCD00013938 |
Formula : | C7H5Cl2NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 190.03 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Danger | Class: | 4.1,6.1 |
Precautionary Statements: | P280-P210-P240-P264-P270-P301+P310-P330-P370+P378-P403+P233-P405-P501 | UN#: | 2926 |
Hazard Statements: | H228-H301-H315-H319-H335-H372 | 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% | With iron oxide; zirconium(IV) chloride; sodium cyanoborohydride In neat (no solvent) at 75 - 80℃; for 1 h; | General procedure: A mixture of benzaldehyde oxime (0.121 g, 1 mmol) and nano Fe3O4 (0.046 g, 0.2 mmol) (nano particle size≈70 nm) was ground in a porcelain mortar. ZrCl4 (0.233 g,1 mmol) was then added and grinding the mixture was continued for a moment at room temperature. The mortar was heated in an oil bath until the temperature of reaction mixture reaches 75–80 °C. NaBH3CN (0.314 g, 5 mmol) wasthen added portion wisely and the mixture was ground for15 min at 75–80 °C. After completion of the reaction, H2O(5 mL) was added and the mixture was stirred for 5 min. The mixture was extracted with EtOAc (2 × 5 mL) and then dried over anhydrous Na2SO4. Evaporation of the solvent affords the pure liquid benzylamine in 93 percent yield (0.1 g, Table 2, entry 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; triphenylphosphine; In acetonitrile; at 20℃; for 0.166667h; | To the mixture of PPh3 (0.525 g, 2 mmol) and TBBDA (0.287 g, 0.53 mmol) in dry acetonitrile (5 mL), 4-nitrobenzaldehyde oxime (0.166 g, 1 mmol) was added. The mixture was stirred at room temperature. The progress of the reaction was monitored by TLC. After completion of the reaction (Table 1), the solvent was evaporated. The crude products were purified by short-column chromatography (packed with silica gel, using n-hexane/ethyl acetate (8:2) as eluent) to achieve the desired 4-nitrobenzonitrile with 0.13 g, 92% yield. |
94% | With (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: In an oven-dried two-necked 50 mLround-bottomed flask, equipped with a stirring bar, a solution of the oxime(1.0 mmol) and 2-NO2-C6H4-SO3XY(1.5 mmol) dissolved in anhydrous CH2Cl2 (5.0 mL) wasplaced under the atmosphere of nitrogen. The reaction mixture was stirred atroom temperature for 5 min, then DBU (2.5 mmol) was added drop wise over 2 min.The reaction mixture became a clear homogeneous solution after addition of DBU.The reaction was monitored by TLC. The reaction mixture was diluted with EtOAcand washed with water (2×5 mL) followed by brine (2×5 mL) upon completeconsumption of the starting material. Product was purified by columnchromatography.Furthermore, the by-product Oxymacould be readily recovered by acidifying the aqueous layer, and then extractingwith ethyl acetate. The Oxyma thus recovered can then be reused to regeneratethe sulfonate ester of Oxyma, which can be further used for a separate batch ofreaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.7% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 40℃; for 1h; | 2,6-dichlorobenzanamine (10.48 g, 0.055 mol, 1.0 eq) was dissolved in 63 ml of DMF and N-chlorosuccinimide (7.36 g, 0.28 mol, 1.0 eq) was added portionwise.And the mixture was stirred at 40 C for 1 h. The reaction solution was finished and cooled to a temperature,Poured into 200 ml of ice water at 0 C, extracted with 200 ml of methyl tert-butyl ether, and the aqueous layer was discarded. The organic layer was washed with brine, dried over anhydrous sodium sulfate, evaporated to dryness at 30 C to form a solid oil. The crystals were triturated with 6 ml of n-hexane to form a solid filter. The filter cake was dried in vacuo to give intermediate 8-1-2,Yellow solid 12.10 g,the yield was 97.7%. |
97.7% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 40℃; for 1h; | 2,6-dichlorobenzylhydroxylamine (10.48 g, 0.055 mol, 1.0 eq) was dissolved in 63 ml N-chlorosuccinimide (7.36 g, 0.28 mol, 1.0 eq) was added portionwise in DMF. After the addition, the mixture was stirred at 40 C for 1 h. The reaction mixture was completed, cooled to room temperature, poured into 200 ml of ice water at 0 C, extracted once with 200 ml of methyl tert-butyl ether, and the aqueous layer was discarded.The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated to drynessThe filter cake was vacuum dried to give Intermediate 8-1-2, 12.10 g of a yellow solid, yield 97.7%. |
97% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 20℃; for 1h; | 2,6-Dichlorobenzaldehyde oxime (26 g) was dissolved in DMF (160 mL).Add NCS (18.5g) in portions at room temperature.After stirring for 1 hour,Pour the solution into water (800 mL),Extracted with ethyl acetate,The ethyl acetate layers were combined and washed with water and saturated brine, respectively.Dry with anhydrous sodium sulfate,The solvent was added to dryness to give 30 g, m. |
97% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 25℃; for 1h; | To a solution of 2 (26.0 g, 0.138 mol) in DMF (160 mL) was slowly added NCS (18.5 g, 0.139 mol) and kept the internal temperature below 25 C. The reaction mixture was stirred for 1 h at room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 3 (30.0 g, 97%) as light yellow oil which was used in the next step without further purification. |
96% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 20℃; for 2h; | To aIL round-bottom flask was addedN-[(2,6-dichlorophenyl) methylidene]hydroxylanrine lb (60 g, 315.74 mmol, 1.0 equiv.), N.N-dimethylformamide (250 mL), andN-chlorosuccinimide (NCS, 42.5 g, 318.28 mmol, 1.0 equiv.). The resulting nrixture was stirred for 2 h at room temperature, and then quenched by the addition of 500 mL of ice/salt.The aqueous mixture was extracted v.ith ethyl acetate (lL x 3) and the combined organiclayers were washed with brine (l L x 3), dried vvith sodium sulfate, filtered and concentratedin vacuo to give result 68 g (96%) of 2,6-dichloro-N-hydroxylbenzene-l-carbonimidoyl5 chloride J c as a white solid. |
94% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 20℃; for 1h; | A solution of 2,6-dichlorobenzaldehyde (25 g, 0.14 mole) in ethanol (200 mL) was added to a solution of hydroxylamine hydrochloride (11 g, 0.16 mole) and sodium hydroxide (6.3 g, 0.16 mole) in water (100 mL). The resulting mixture was stirred at 90° C. for 24 hours. The volume was reduced in vacuo by ca 30 mL which induced a precipitate. The flask was then cooled to room temperature and the white solids were collected by filtration and washed with water (2 100 mL). Yield=25.9 g. (96%) of <strong>[25185-95-9]2,6-dichlorobenzaldehyde oxime</strong>. A 500 mL round bottom flask was charged with a solution of <strong>[25185-95-9]2,6-dichlorobenzaldehyde oxime</strong> (13 g, 0.07 mole) in N,N-dimethyl formamide (150 mL). The flask was placed in an ambient temperature water bath. The flask was then charged with N-chlorosuccinimide (9.2 g, 0.07 mole). Within minutes of dissolution, an exotherm was observed along with a significant color change to dark yellow. The reaction was stirred an additional hour then the contents were then poured into water (200 mL) and the product extracted with diethyl ether (300 mL). The ethereal layer was washed with water (3 100 mL) and brine (50 mL), then dried over anhydrous magnesium sulfate. After filtering, the solvent was removed in vacuo to yield 14.5 g of a yellow oil. (94%) of 2,6-dichlorophenyl hydroximic chloride which was used without further purification. A stirred solution of methyl isobutyryl acetate (2 g, 15.6 mmol) in tetrahydrofuran (15 mL) was treated with a solution of sodium methoxide (31.5 mL, 0.5 M in methanol) followed by a solution of 2,6-dichlorophenyl hydroximic chloride (3.5 g, 15.6 mmol) in tetrahydrofuran (5 mL). After stirring at ambient temp 16 h the solvent was removed in vacuo. The resulting residue was partitioned with diethyl ether (100 mL) and water (100 mL). The ethereal layer was washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered and condensed to an oil. The product was purified by flash chromatography on silica gel using 10% ethyl acetate in hexane as mobile phase. Yield=3.1 g. (62%) of 3-(2,6-dichlorophenyl)-4-carbomethoxy-5-isopropyl-isoxazole. |
94% | With N-chloro-succinimide; N,N-dimethyl-formamide; at 40℃; | 2,6-Dichlorobenzaldehyde oxime (12.0 g, 63.1 mmol) was dissolved in DMF (45.9 mL) and heated to 40 C. NCS (10.1 g, 76.0 mmol) dissolved in DMF (38.3 mL) was then added to the warm solution over the space of approximately 3 minutes. After stirring overnight the reaction mixture was cooled to room temperature, poured into ice, and extracted with Et^O. The organic layer was collected and washed with brine. The combined aqueous layers were back extracted with Et20. The combined organic layers were dried over Na2S04, filtered and concentrated to dryness in vacuo. The residue was purified by flash chromatography on SiC (0-50% EtOAc/hexanes, Isco 120 g column) to give 2,6- dichloro-N-hydroxybenzimidoyl chloride (13.3 g, 59.3 mmol, 94% yield) as a waxy white solid. NMR (500 MHz, CDCh) δ 8.02 (s, 1H), 7.43-7.37 (m, 2H), 7.37-7.30 (m, 1H). |
94% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 40℃; | 2,6-Dichlorobenzaldehyde oxime (12.0 g, 63.1 mmol) was dissolved in DMF (45.9 mL) and heated to 40 C. NCS (10.1 g, 76.0 mmol) dissolved in DMF (38.3 mL) was added to the warm solution over the space of approximately 3 minutes. After stirring overnight the reaction mixture was cooled to room temperature, poured into ice, and extracted with Et20. The organic layer was collected and washed with brine. The combined aqueous layers were back extracted with Et20. The combined organic layers were dried over Na2SO4, filtered and concentrated to dryness in vacuo. The residue was purified by flash chromatography on Si02 (0-50% EtOAc/hexanes, Isco 120 g column) to give 2,6-dichloro-N-hydroxybenzimidoyl chloride (13.3 g, 59.3 mmol, 94% yield) as a waxy white solid. ‘H NMR (500 MI-Tz, CDC13) ö 8.02 (s, 1H), 7.43-7.37 (m, 2H), 7.37-7.30 (m, 1H). |
94% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 40℃; | 2,6-Dichlorobenzaldehyde oxime (12.0 g, 63.1 mmol) was dissolved in DMF (45.9 mL) and heated to 40C. NCS (10.1 g, 76.0 mmol) dissolved in DMF (38.3 mL) was then added to the warm solution over the space of approximately 3 minutes. After stirring overnight at 40C. the reaction mixture was cooled to room temperature, poured into ice, and extracted with Et2O. The organic layer was collected and washed with brine. The combined aqueous layers were back extracted with Et2O. The combined organic layers were dried over Na2SO4, filtered and concentrated to dryness in vacuo. The residue was purified by flash chromatography on SiO2 (0-50% EtOAc/hexanes, Isco 120 g column) to give 2,6-dichloro-N-hydroxybenzimidoyl chloride (13.3 g, 59.3 mmol, 94% yield) as a waxy white solid. 1H NMR (500 MHz, CDCl3) δ 8.02 (s, 1H), 7.43-7.37 (m, 2H), 7.37-7.30 (m, 1H). |
90% | With N-chloro-succinimide; In N,N-dimethyl-formamide; for 2h; | N-chlorosuccinimide (19.06 g, 0.1428 mol) was added portion wise to a solution of 2, 6-dichlorobenzaldehyde oxime (27 g, 0.1428 mole) in DMF (300 ml). After 2h the reaction was poured into water and the product extracted with ethyl acetate. The combined organic layers were washed with water, brine and dried over anhydrous sodium sulfate. After filtering, the solvent was removed under reduced pressure to afford the titled compound as yellow oil (29 g, 90 %). 1H NMR (400 MHz, d6-DMSO): d 12.68 (s, 1H), 7.72-7.52 (m, 3H). |
80% | With N-chloro-succinimide; In N,N-dimethyl-formamide; | Take 2,6-dichlorobenzyloxime 13g (70 mmol) in 250 mL two bottles,Add 150 mL of DMF dissolved,Then 9.2 g NCS (70 mmol) was added in portions.Plus finished, continue to respond 2-3h,TLC showed complete reaction.The system was then added to 200 mL of ice water,There will be needle-like solid production,Ethyl acetate was added,Saturated sodium chloride wash,Dried over anhydrous sodium sulfate to give about 12 g of product 2,6_dichlorobenzyloxymethoxime (80%) |
75% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 40 - 45℃; for 3.5 - 7h;Product distribution / selectivity; | Step 2; 2,6-Dichloro-benzaldehyde chloro-oxime; <n="57"/>N-Chlorosuccinimide (1162g, 8.53mol) in DMF (4.5L) is added dropwise over a solution of 2,6-dichloro-benzaldehyde oxime (1621.78g, 8.53mol) in DMF (5.3L) heated at 4O0C (addition is complete in about 6 hours). The mixture is stirred for Ih at that temperature. The reaction is cooled at room temperature, poured onto H2O (30L) at O0C, and extracted with MTBE (36L) and the aqueous phase was discarded. The organic layer is washed with brine, dried over Na2SO4, filtered and evaporated to dryness (at 3O0C). The crude, as a solid-oil, is triturated in IL of hexane and the solid formed is filtered and dried under vacuum to obtain the desired compound (1440.9g, 75% yield). MS (m/e): 224 (M+l). Alternate Procedure: Add a solution of N-chlorosuccinimide (8.4 g, 62.8 mmol) in DMF (33 mL) to a 42 0C solution of 2,6-dichloro-benzaldehyde oxime (217 g, 1.14 mol) in DMF (700 mL). Stir for 30 minutes and then add a solution of N- chlorosuccinimide (159 g, 1.19 mol) in DMF (617 mL) while maintaining the temperature between 40 0C and 45 0C. Stir for 1 hour. Cool to room temperature and stir for 2 h. The resulting solution of the title compound is used directly |
With N-chloro-succinimide; In N,N-dimethyl-formamide; at 5 - 20℃; for 1 - 1.33333h;Product distribution / selectivity; | 6b) Ethyl 5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate To a solution of <strong>[25185-95-9]2,6-dichlorobenzaldehyde oxime</strong> (3.73 g, 19.6 mmol) in N,N-dimethylformamide (12 mL) was added solid N-chlorosuccinimide (2.62 g, 19.6 mmol). The solution was stirred for approximately 1 hour and the poured into water and extracted twice with ether. The combined organic layers containing the crude imidoyl chloride were dried over magnesium sulfate and concentrated. To a solution of ethyl 3-cyclopentyl-3-oxopropanoate (4.34 g, 23.6 mmol) in tetrahydrofuran (5 mL) at 0 C. was added a 25 wt % solution of sodium ethoxide in ethanol (7.4 mL, 24 mmol) quickly. The above imidoyl chloride was added. A solid was seen to precipitate. The mixture was allowed to warm to ambient temperature and stir overnight. The mixture was then poured into water and extracted three times with ethyl acetate and the combined organic layers were dried over magnesium sulfate, concentrated and the residue purified by chromatography (silica gel 5% ethyl acetate in hexanes) to afford ethyl 5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate (3.04 g, 43%). 1H-NMR (400 MHz, DMSO-d6) δ 7.63-7.53 (m, 3H), 4.02 (q, J=7 Hz, 2H), 3.92-3.84 (m, 1H), 2.14-2.06 (m, 2H), 1.84-1.64 (m, 6H), 0.91 (t, J=5 Hz, 3H).; 7a) Ethyl 5-cyclobutyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate To a water bath-cooled solution of <strong>[25185-95-9]2,6-dichlorobenzaldehyde oxime</strong> (2.20 g, 11.6 mmol) in N,N-dimethylformamide (7 mL) was added solid N-chlorosuccinimide (1.55 g, 11.6 mmol). The solution was stirred while in the water bath for approximately 20 min and outside the bath for approximately 1 hr. The solution was poured into water and extracted twice with ether. The combined organic layers containing the crude imidoyl chloride were dried over magnesium sulfate and then concentrated. To a separate solution of ethyl 3-cyclobutyl-3-oxopropanoate (2.37 g, 13.9 mmol) in THF (3 mL) at 0 C. was added sodium ethoxide (25 wt % in ethanol, 4.36 mL, 13.9 mmol). The solution was stirred for a few minutes and then the above imidoyl chloride was added. The solution was stirred at 0 C. for 10 minutes and then at ambient temperature overnight. The solution was poured into water and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, concentrated and purified by chromatography (silica gel, 0-5% ethyl acetate in hexanes gradient elution) to afford ethyl 5-cyclobutyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate (1.52 g, 38%). 1H-NMR (400 MHz, DMSO-d6) δ 7.63-7.53 (m, 3H), 4.29-4.20 (m, 1H), 4.02 (q, J=7 Hz, 2H), 2.43-2.36 (m, 4H), 2.15-2.06 (m, 1H), 1.97-1.89 (m, 1H), 0.94 (t, J=7 Hz, 3H).10b) Ethyl 5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate To a water bath-cooled solution of <strong>[25185-95-9]2,6-dichlorobenzaldehyde oxime</strong> (2.20 g, 11.6 mmol) in N,N-dimethylformamide (7 mL) was added solid N-chlorosuccinimide (1.55 g, 11.6 mmol). The solutions were stirred while in the water bath for approximately 20 min and the outside the bath for approximately 1 hour. The solution was poured into water and extracted twice with ether. The combined organic layers containing the crude imidoyl chloride were dried over magnesium sulfate and then concentrated. To a separate solution of ethyl 3-cyclopropyl-3-oxopropanoate (2.17 g, 13.9 mmol) in THF (3 mL) at 0 C. was added sodium ethoxide (25 wt % in ethanol, 4.36 mL, 13.9 mmol). The solution was stirred for a few minutes and then the above imidoyl chloride was added. The solution was stirred at 0 C. for 10 minutes and then at ambient temperature overnight. The solution was poured into water and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, concentrated and purified by chromatography (silica gel, 0-5% ethyl acetate in hexanes gradient elution) to afford ethyl 5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate (289 mg, 8%). 1H-NMR (400 MHz, DMSO-d6) δ 7.62-7.53 (m, 3H), 4.04 (q, J=7 Hz, 2H), 2.84-2.82 (m, 1H), 1.35-1.25 (m, 4H), 0.93 (t, J=7 Hz, 3H).; 13b) {3-(2,6-Dichlorophenyl)-5-[(1S)-1-methylpropyl]-4-isoxazolyl}methanol To a solution of <strong>[25185-95-9]2,6-dichlorobenzaldehyde oxime</strong> (26.4 g, 139 mmol) in N,N-dimethylformamide (70 mL) at 5 C. was added solid N-chlorosuccinimide (18.6 g, 139 mmol) in portions. The mixture was allowed to stir and warm to ambient temperature (with occasional cooling when warming was noted) over approximately 1.5 hour and then poured into ether. The ether layer containing the crude imidoyl chloride was washed twice with water followed by brine, dried over magnesium sulfate and concentrated. To a separate solution of ethyl 4-methyl-3-oxohexanoate (28.8 g, 167 mmol) in tetrahydrofuran (50 mL) at 0 C. was added sodium ethoxide (21 wt % in ethanol, 62.3 mL, 167 mmol) quickly. Then the above imidoyl chloride was added dropwise in tetrahydrofuran (100 mL). The solution was allowed to stir while warming to ambient temperature overnight. The mixtur... | |
With N-chloro-succinimide; In DMF (N,N-dimethyl-formamide); at 20℃; | A solution of 2, 6-DICHLOROBENZALDEHYDE oxime (19. 8g, 0.104 mol) in N, N-dimethyl formamide (80 mL) was placed in an ambient temperature water bath and was treated with N-CHLOROSUCCINIMIDE (13.9g, 0.104 mole). Following dissolution, an exotherm was observed along with a color change to dark yellow. The reaction was stirred an additional hour then the contents were then poured into water (200 mL) and the product extracted with diethyl ether (300mL). The ethereal layer was washed with water (3x 100 mL) and brine (50mL), then dried over anhydrous magnesium sulfate. After filtering, the solvent was removed in vacuo to yield a yellow oil which was used in the next step without further purification. Separately, a solution of methyl isobutyryl acetate (18g, 0.125 mol) in tetrahydrofuran (25 mL) at 0C was treated with a solution of sodium methoxide (250 mL, 0.5 M in methanol). A solution of the above crude 2, 6-DICHLORO-N-HYDROXYBENZENECARBOXIMIDOYL chloride in tetrahydrofuran (80 mL) was then added dropwise. After stirring at ambient temperature for 16h the solvent was removed in vacuo. The residue was triturated with water (250 mL) and the resulting solids filtered and washed with water. Yield = 22.7 g. (69%) of methyl 3- (2, 6-dichlorophenyl)-5-isopropylisoxazole-4-carboxylate. | |
With N-chloro-succinimide; In DMF (N,N-dimethyl-formamide); at 40 - 50℃; for 0.5h; | THE GENERAL PROCEDURE OF R. K. HOWE ET AL, J. ORS. CHEM., 1980, 45,3916-3918 WAS followed. 2,6-Dichlorobenzaldoxime (25.1 gm, 0.132 mol) was dissolved in DMF (150 mL). Then N-chlorosuccinimide (approximately 1.5 g) was added. After several minutes the reaction was heated until the internal temperature reached 50 C. Then the remainder of the N-chlorosuccinimide was added in small portions to a total of 17.6 g (0.132 mol), keeping the reaction temperature at 40-50 C. After the addition was complete, the reaction was allowed to stir for 0. 5H, then was diluted with 600 mL of water. The mixture was extracted twice with ether. The combined ether extracts were washed three times with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was concentrated under vacuum to give the title a-chlorooxime as a white solid (m. p. 89-90 C). NMR (300 MHz, CDC13) : 7.98 (s, 1H, exchanges with D20), 7.3-7. 4 ppm (m, 3H).Again referring to FIG. 3A, the general procedure described by R. K. Howe, et al, J. P ORG. CHEM., 1980,45, 3916-3918 WAS FOLLOWED. THE OXIME WAS DISSOLVED IN DMF AND 0.1 molar equivalent of N-chlorosuccinimide was added and the mixture was heated to 50 C to initiate the reaction. The remaining 0.9 molar equivalent of N-CHLOROSUCCINIMIDE was added in small portions keeping the reaction temperature under 50 C. After the addition was completed, the mixture was stirred for 0. 5h and then diluted with water. The mixture was extracted with ether and the combined ether extracts were washed with water and brine. The ether layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield the desired α-chlorooxime 247 | |
With hydrogenchloride; N-chloro-succinimide; In N,N-dimethyl-formamide;Product distribution / selectivity; | Intermediate Preparation 3; 2,5 Dichlorobenzaldehyde-chloro-oxime; 2,6-Dichloro-benzaldehyde oxime (7.6 g, 40 mmol) is dissolved in 56 mL of DMF and N-chlorosuccinimide (5.9 g, 44.0 mmol) is added followed by a catalytic amount of HCl gas. The reaction mixture is stirred overnight. The reaction mixture is partitioned between ether and water. The layers are separated and the ether layer is washed with brine and is dried over sodium sulfate. The ether layer is filtered and the solvent is removed under reduced pressure to yield the crude product. The crude product is purified via chromatography using a gradient of 10 % ethyl acetate in hexanes to 15% ethyl acetate in hexanes to yield the title compound. 1H-NMR (400MHz, CDCl3) δ 8.76 (broad, IH), 7.38-7.26 (m,3H) | |
With N-chloro-succinimide; In N,N-dimethyl-formamide; at 20℃; for 1h; | A 500 mL round bottom flask was charged with a solution of compound A2a (25.9 g, 0.14 mol) in 300 ml_ of DMF. The flask was placed in an ambient temperature water bath. The flask was then charged with NCS (18.4 g, 0.14 mol). The reaction was stirred an additional hour, then the contents was poured into 400 mL of water and the product was extracted with 500 mL of Et2O. The organic layer was washed with water (2 x 200 mL) and 100 mL of brine, then dried over MgSO4. After filtration, the solvent was removed under reduced pressure to give 29 g of compound A3a as a yellow oil which was used into the following reaction without further purification. | |
With hydrogenchloride; N-chloro-succinimide; In dichloromethane; water; at 20℃; for 4h; | General procedure: To a stirred solution of oxime (1.3 mmol) in CH2Cl2 (10 mL) (or in DMF for pyridine-2-carboxaldoxime) at room temperature was added solid NCS (0.187 g, 1.4 mmol). The reaction was initiated by the addition of one drop of concd hydrochloric acid. After stirring for 4 h, the solution of hydroximoyl chloride in CH2Cl2 (or in DMF) was used in the cycloaddition. Yield >98%. | |
26 g | With N-chloro-succinimide; In chloroform; at 20℃; for 4h; | N-chlorosuccinimide(NCS, 18.4g, 140mmol) was added to a solution of the intermediate compound(Step 1)(25.9g, 140mmol) in chloroform(1000ml) and stirred for 4 hours at room temperature. The reaction mixture was evaporated in vacuum, diluted with dicholrometane and washed with water. The combined organic layers were dried over MgSO 4, filtered, evaporated in vacuum and purified using silica chromatography to afford the intermediate compound 2,6-dichloro-N-hydroxybenzimidoyl chloride(29g) without any further purification |
5.5 g | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 20℃; for 1h; | 2,6-Dichlorobenzaldehyde oxime (4.7 g, 24.7 mmol) is dissolved in DMF (40 mL), followed by adding NCS (3.3 g, 24.7 mmol), and the mixture is stirred at room temperature for 1 hr. After that, water (100 mL) is poured into the reaction mixture, and then the mixture is extracted with diethyl ether (2 * 150 mL), the organic solution is combined and washed with saturated salt water (3 * 100 mL), followed by adding anhydrous Na2SO4 for drying , and subsequently the resulted product is filtered and rotated to dryness. Finally, 5.5 g of yellow oily matter, 2,6-dichloro-N-hydroxybenzimidoyl chloride is obtained and it is directly used in the next step without purification. |
With N-chloro-succinimide; In chloroform; at 20℃; for 4h; | The intermediate compound (25.9 g, 140 mmol) prepared in the above step 1 was dissolved in chloroform (1000 ml)N-chlorosuccinimide (NCS, 18.4 g, 140 mmol) was added thereto, followed by stirring at room temperature for 4 hours.The reaction mixture was concentrated, diluted with dichloromethane and washed with distilled water.Dried with magnesium sulfate, Filtration and concentration afforded the intermediate compoundTo give 2,6-dichloro-N-hydroxybenzimidoyl chloride (29 g)Was used in the next reaction without further purification. | |
With N-chloro-succinimide; In N,N-dimethyl-formamide; at 20℃; for 2h; | To a 1 L round-bottom flask was added N-[(2,6-dichlorophenyl) methylidene]hydroxylamine lb (60 g, 3 15.74 mmol, 1.0 equiv.), N,N-dimethylformamide (250 mL), and N-chl orosucci nimide (42.5 g, 318.28 mmol, 1.0 equiv.). The resulting mixture was stirred for 2 h at RT and then quenched by with ice/brine (500 mL). The aqueous mixture was extracted with EtOAc (1 L x 3), The combined organic layers were washed with brine ( 1 L x 3), and concentrated in vacuo to give 2,6-dichloro-N-hydroxylbenzene-l-carbonimidoyl chloride lc (68 g, 96%) as a white solid. The product was carried onto the next step without further purification. | |
88.6 g | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 40℃; for 1h; | 2,6-Dichloro-benzaldehyde oxime (100g, 0.526mol) was dissolved in DMF (N, N-dimethylformamide, 200mL),willChlorosuccinimide (70.3 g, 0.526 mol) was dissolved in 100 mL of DMF and dropped into the above 2,6-dichloro-benzaldehyde oxime solution at 40 C, and then reacted at 40 C for 1 hour.The reaction was monitored by thin layer chromatography (TLC). After the reaction was completed, the reaction was cooled to room temperature, and a large amount of water and ethyl acetate (EA) were added for extraction.The organic layer was washed three times with 200 mL of water, and the organic layer was washed with 200 mL of saturated saline, dried over anhydrous Na2SO4, and the organic layer was spin-dried.A crude product was obtained, and 100 ml of hexane was added for grinding, suction filtration, and drying.88.6 g of a solid was obtained as 2,6-dichloro-benzaldehyde-chloro-oxime. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With iron oxide; zirconium(IV) chloride; sodium cyanoborohydride; In neat (no solvent); at 75 - 80℃; for 1h; | General procedure: A mixture of benzaldehyde oxime (0.121 g, 1 mmol) and nano Fe3O4 (0.046 g, 0.2 mmol) (nano particle size≈70 nm) was ground in a porcelain mortar. ZrCl4 (0.233 g,1 mmol) was then added and grinding the mixture was continued for a moment at room temperature. The mortar was heated in an oil bath until the temperature of reaction mixture reaches 75-80 C. NaBH3CN (0.314 g, 5 mmol) wasthen added portion wisely and the mixture was ground for15 min at 75-80 C. After completion of the reaction, H2O(5 mL) was added and the mixture was stirred for 5 min. The mixture was extracted with EtOAc (2 × 5 mL) and then dried over anhydrous Na2SO4. Evaporation of the solvent affords the pure liquid benzylamine in 93 % yield (0.1 g, Table 2, entry 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With pyridine; N-chloro-succinimide; In dichloromethane; at 0℃; for 0.5h; | Oxime b (23 gm, 0.122 moles, 1 eq) was dissolved in DCM (250 ml) and to this N-chlorosuccinimide (19.6 gm, 0.1464 moles, 1.2 eq) was added at 00C followed by the addition of pyridine (13.5 gm, 0.1708 moles, 1.4 eq). The reaction mixture was stirred at 00C for 30 minutes and monitored by TLC. The reaction mass was washed with H2O (500 ml) and the DCM layer was separated, dried over Na2SO4, concentrated and purified immediately by fast column (silica gel, 60-120 mesh, 3-5% EA/hexane). Pale yellow solid of N-oxide c was obtained in 61% yield (14 gm) and used immediately for the next reaction. All the concentrations were done below 45 0C and any increase in the temperature resulted in the decomposition of N-oxide. |
61% | With pyridine; N-chloro-succinimide; In dichloromethane; at 0℃; for 0.5h; | Oxime b (23 gm, 0.122 moles, 1 eq) was dissolved in DCM (250 ml) and to this N-chlorosuccinimide (19.6 gm, 0.1464 moles, 1.2 eq) was added at 00C followed by the addition of pyridine (13.5 gm, 0.1708 moles, 1.4 eq). The reaction mixture was stirred at 00C for 30 minutes and monitored by TLC. The reaction mass was washed with H2O (500 ml) and the DCM layer was separated, dried over Na2SO4, concentrated and purified immediately by fast column (silica gel, 60-120 mesh, 3-5% EA/hexane). Pale yellow solid of N-oxide c was obtained in 61% yield (14 gm) and used immediately for the next reaction. All the concentrations were done below 45 0C and any increase in the temperature resulted in the decomposition of N-oxide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-chloro-succinimide; In DMF (N,N-dimethyl-formamide); at 40 - 50℃; for 0.5h; | 7.1. 1 Synthesis of 5-Dichloromethyl-3- [4- [3'- (2', 6'- dichlorophenyl)-5'-isoxazolyl] phenyl]-1, 2,4-oxadiazole (See Figure 1); Synthesis of 2, 6-Dichloro-N-hydroxybenzenecarboximidoyl Chloride; The general procedure of R. K. Howe, et al, J. Org. Chem., 1980,45, 3916- 3918 was followed. 2,6-Dichlorobenzaldoxime (25.1 gm, 0.132 mol) was dissolved in dimethylformamide (150 mL). ThenN-chlorosuccinimide (approximately 1.5 g) was added. After several minutes the reaction was heated until the internal temperature reached 50 C. Then the remainder of the N-chlorosuccinimide was added in small portions to a total of 17.6 g (0.132 mol), keeping the reaction temperature at 40-50 C. After the addition was complete, the reaction was allowed to stir for 0. 5h, then was diluted with 600 mL of water. The mixture was extracted twice with ether. The combined ether extracts were washed three times with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was concentrated under reduced pressure to give the title a-chlorooxime as a white solid (m. p. 89-90 C). NMR (300 MHz, CDC13) : 7.98 (s, 1H, exchanges with D20), 7.3-7. 4 ppm (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-chloro-succinimide;hydrogenchloride; In N,N-dimethyl-formamide; | Step 2 2.6 Dichloro-benzaldehvde chloroximeTo a solution of 2,6-dichloro-benzaldehyde (7.6 g,40 mmol) in DMF (56 mL) is addedN- chlorosuccinimide (5.9 g,44.0 mmol) followed by a catalytic amount of HCl gas. The reaction mixture is stirred overnight. The reaction mixture is partitioned between ether and water. The layers are separated and the ether layer is washed with brine and dried over sodium sulfate. The ether layer is filtered and the solvent is removed under reduced pressure to yield the crude product. The crude product is chromatographed using a gradient of 10 % ethyl acetate in hexanes to 15% ethyl acetate in hexanes to yield the title compound. 1H-NMR (400MHz, CDCl3) δ 8.76(b,lH), 7.38-7.26(m,3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | To a solution of 2,6-dichlorobenzaldehyde oxime (2.2 g, 11.6 mmol) in N9N,- dimethylformamide (7 mL) cooled in a water bath was added solid N-chlorosuccinimide (1.5 g, 11.6 mmol). The solution was stirred with the flask in the water bath for approximately 20 minutes and then with the flask out of the bath for approximately 1 hour. The solution was poured into water and then extracted twice with ether. The combined organic phases were dried over magnesium sulfate and concentrated. To a separate solution of <strong>[24922-01-8]ethyl 3-cyclobutyl-3-oxopropanoate</strong> (2.4 g, 13.9 mmol) in tetrahydrofuran (3 mL) at 0 0C was added a 3.16 M solution of sodium ethoxide in ethanol (4.4 mL, 13.9 mmol) quickly. The solution was stirred for a few minutes. To that solution was added the isolated imidoyl chloride in tetrahydrofuran (5 mL) dropwise. The solution was stirred at 0 0C for approximately Ih and then allowed to stir at ambient temperature overnight. The solution was poured into water and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, concentrated and purified by chromatography (silica gel, 0-5% ethyl acetate in hexanes gradient elution) to afford a white solid (1.5 g, 38%). 1H-NMR (DMSO-^15) delta 7.63 - 7.53 (m, 3H), 4.25 (quintet, J = 9 Hz, IH), 4.02 (q, J = 7 Hz, 2H)9 2.43 - 2.36 (m, 4H), 2.15 - 1.89 (m, 2H), 0.94 (t, J = 7 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With triethylammonium acetate; at 20℃; for 2h; | General procedure: To a stirred solution of 2-naphthol (0.2 mmol) in TEAA(2 ml), was added acetic anhydride (0.22 mmol). The solutionwas stirred for 3 hours at room temperature. After consumptionof starting material (TLC monitoring, ethyl acetate/hexane, 2:8), the product formed was diluted with 1 mlH2O and extracted with 3 x 2 ml ether. The combined organiclayer was separated, dried (Na2SO4), and evaporatedunder reduced pressure to afford the desired product. 1H and13C NMR spectra were in full accordance with the structureproposed. The water in the aqueous layer was distilled under reduced pressure leaving behind the TEAA which was furtherrecycled. |
Tags: 25185-95-9 synthesis path| 25185-95-9 SDS| 25185-95-9 COA| 25185-95-9 purity| 25185-95-9 application| 25185-95-9 NMR| 25185-95-9 COA| 25185-95-9 structure
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