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[ CAS No. 53064-54-3 ] {[proInfo.proName]}

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Chemical Structure| 53064-54-3
Chemical Structure| 53064-54-3
Structure of 53064-54-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 53064-54-3 ]

CAS No. :53064-54-3 MDL No. :MFCD16112235
Formula : C4H2ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 131.52 Pubchem ID :-
Synonyms :

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Precautionary Statements: UN#:
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Application In Synthesis of [ 53064-54-3 ]

* 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.

  • Downstream synthetic route of [ 53064-54-3 ]

[ 53064-54-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 3209-71-0 ]
  • [ 53064-54-3 ]
YieldReaction ConditionsOperation in experiment
4.80 kg With oxalyl dichloride; In N,N-dimethyl-formamide; toluene; at 20 - 95℃;Inert atmosphere; Large scale; [00226] Isooxazole-3 -carboxylic acid ((8'), 92 wt % assay based on 1H-NMR, 3.86 kg, 34.1 mol, 1.0 equiv), toluene (19.3 L) and DMF (0.131 L, 1.69 mol, 0.05 equiv) were mixed in a 30 L jacketed reaction vessel equipped with a nitrogen inlet-outlet, overhead stirrer, a thermocouple and an addition funnel. The resulting slurry was heated to 45 to 55 C. Oxalyl chloride (4.80 kg, 37.8 mol, 1.11 equiv) was charged via the addition funnel over the course of 4 hours 30 minutes, while maintaining the reaction temperature between 45 to 55 C. Vigorous gas evolution was observed. A brown mixture was obtained after the addition. The brown mixture was held at 45 to 55 C for 30 minutes, then heated to 85 to 95 C and stirred at 85 to 95 C for 1 hour. During heating, the brown mixture turned into a black mixture. The black mixture was cooled to 20 to 25 C, over 4 hours and held at 20 to 25 C for a minimum of 16 hours. The reaction was monitored by quenching a portion of the reaction mixture into piperidine and monitoring the formation of the piperidine amide by HPLC ((8') : piperidine amide area:area % was < 1.9). After the reaction was complete by HPLC the dark mixture was in-line filtered via gas a dispersion tube (coarse frit) into a 20 L rotavapor flask. Toluene (3.9 L) was used to rinse the reactor and the rinse was in-line filtered into the 20 L rotavapor flask. The filtered reaction mixture was concentrated under reduced pressure until no more distillate was seen coming off.
  • 2
  • [ 26214-65-3 ]
  • [ 7031-27-8 ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-hydroxymethyl-2-oxazolidinone [ No CAS ]
  • [ 38870-89-2 ]
  • [ 2251-50-5 ]
  • [ 39637-99-5 ]
  • [ 10313-60-7 ]
  • [ 4023-34-1 ]
  • [ 53064-54-3 ]
  • [ 5538-51-2 ]
  • [ 157373-08-5 ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(2-methoxyacetyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(cyclopropanecarbonyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(furan-3-carbonyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(isoxazole-3-carbonyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(2-(phenylthio)acetyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(3,4-dimethoxybenzoyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(2-acetoxybenzoyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(2,3,4-trifluorobenzoyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(perfluorobenzoyloxy)methyl-2-oxazolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pyridine; dichloromethane at 20℃; Combinatorial reaction / High throughput screening (HTS); 3 To about 295 mg (1.0 mmoles) of (S)-3- (2,5-dimethocyphenacyl) -5- hydroxymethyl-2-oxazolidinone in dry CH2Cl2 (8 mL CH2Cl2), 1.0 equiv. (1.1 mmoles) of pyridine was added and the reaction mixture stirred at room temperature. To this reaction mixture was added 1.0 equiv. of a mixture of ten different acetyl chlorides. The reaction was stirred overnight at room temperature. Afterwards, TLC of an aliquot indicated that complete conversion of the (S)-3- (2,5-dimethocyphenacyl) -5- hydroxymethyl-2-oxazolidinone to (S)-3- (2,5- dimethocyphenacyl)-5- (substituted methyl) -2- oxazolidinone had occurred. Therefore, about 3 mL of 20% NH4Cl was added to the reaction mixture and the organic layer removed and saved. The aqueous layer was extracted two times with 40 mL aliquots of CH2Cl2. The CH2Cl2 extracts were combined with the saved organic layer and the mixture dried with 2.5 g anhydrous Na2SO4. The mixture was then concentrated in vacuo to provide a crude product. The crude product was analyzed by 1H-NMR, 13C NMR, HPLC, and TLC using a EtOAc: hexane (2: 1) solvent system. An HPLC profile of the (S)-3- (2,5- dimethocyphenacyl)-5- (substituted methyl) -2- oxazolidinone products made is shown in Figure 3. The products represented by the peaks in the HPLC are shown in Figure 4. This example illustrates the principle of the present invention. As shown by this example, providing n=10 acetyl halides in a single reaction produces 10 (S)-3- (2,5-dimethocyphenacyl) -5- (substituted methyl) -2-oxazolidinone products. If n=10 aryl bromides had been used as well to arylate the N at the 3-position, the process would have generated 100 (S)-3- (substituted)-5- (substituted methyl) -2-oxazolidinone products.
  • 3
  • [ 915720-54-6 ]
  • [ 1216246-45-5 ]
  • [ 53064-54-3 ]
  • [ 1446359-15-4 ]
YieldReaction ConditionsOperation in experiment
13% Stage #1: 1-(5-fluoropyridin-2-yl)ethan-1-one With lithium hexamethyldisilazane In toluene at 0℃; for 0.0833333h; Stage #2: isoxazole-3-carbonyl chloride In toluene at 25℃; for 0.0833333h; Stage #3: (2-fluorobenzyl)hydrazine hydrochloride salt With hydrogenchloride In ethanol; toluene at 100℃; for 2h; 1 Compound 32 To a cold solution of l-(5-fluoropyridin-2-yl)ethanone (1 equiv.) in toluene (9.6 ml) at 0 °C, was added 1M LiHMDS in toluene (1 equiv.). The mixture was stirred at 0 °C for 5 min. To this mixture, was added a solution of isoxazole-3-carbonyl chloride (1 equiv.) in toluene (4.8 ml). The mixture was removed from the ice bath and stirred at 25 °C for 5 min. To this mixture, were added 6 N HC1 (1 equiv.), followed by (2-fluorobenzyl)hydrazine hydrochloride (1 equiv.) and ethanol (5 ml). The mixture was heated to 100 °C for 2 h. The mixture was cooled to 25 °C and concentrated under vacuum to give a thick red oil. The oil was purified by column chromatography (0 to 35% ethyl acetate in hexanes) to give 3-(l-(2- fluorobenzyl)-3-(5-fluoropyridin-2-yl)-lH-pyrazol-5-yl)isoxazole (13 % yield) as a clear film and its regioisomer 3-(l-(2-fluorobenzyl)-5-(5-fluoropyridin-2-yl)-lH-pyrazol-3-yl)isoxazole (14 % yield) as a white solid. Compound 32: 1H NMR (400 MHz, CHLOROFORM-^ δ ppm 8.49-8.40 (m, 2 H) 7.96- 8.07 (m, 1 H) 7.37-7.49 (m, 1 H) 7.15-7.24 (m, 1 H) 6.95-7.13 (m, 2 H) 6.84-6.92 (m, 1 H) 6.58 (d, 1 H) 5.93 (s, 2 H).
  • 4
  • [ 6638-79-5 ]
  • [ 53064-54-3 ]
  • [ 189096-90-0 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In dichloromethane; water at -10 - 25℃; Large scale; 1.d Step d): Coupling of Compound (8') and N,O-Dimethylhydroxylamine to provide N- methoxy-N-methylisoxazole-3-carboxamide (1'). [00227] Separately, potassium carbonate (7.06 kg, 51.1 mol, 1.5 equiv) and water (31 L) were stirred in a 100 L jacketed reactor. The reaction solution was cooled to -10 to 10 °C. A <9 - d i m c t h y 1 h y d o x y 1 a m i n c hydrochloride (3.93 kg, 40.3 mol, 1.18 equiv) was charged to the reactor followed by dichloromethane (39 L). The reaction mixture was cooled to -10 to 0 °C. The acyl chloride intermediate formed above (4.4 kg) was charged to a 100 L jacketed reactor containing N,O-dimethylhydroxylamine in dichloromethane, with stirring rate set at 210 RPM, while maintaining the reaction temperature between -10 to 0 °C, over 30 minutes. The addition was a little exothermic, and a brown mixture was obtained after the addition. The reaction mixture was stirred at -10 to 0 °C for 20 minutes, then warmed to 15 to 25 °C and stirred for 10 minutes at this temperature. The layers were separated. The bottom organic layer was collected, and the top aqueous layer was extracted with dichloromethane (7.7 L). The combined organic layers were transferred to a 100 L jacketed reactor and washed with a 15 wt % aqueous sodium chloride solution (11.6 L). The layers were separated. The bottom organic layer was collected, and the top aqueous layer was extracted with dichloromethane (3.9 L). The combined organic layers were concentrated under reduced pressure until no more distillate was seen coming off. Tetrahydrofuran (7.7 L) was charged to this dark oil and the resulting mixture concentrated under reduced pressure to furnish intermediate (1') as a dark oil (4.6 kg, 83 % corrected yield for THF, 4 wt % THF content by 1H-NMR, 0.01 wt % water content by Karl- Fisher (KF) analysis, 98.9 % pure by HPLC). 1H-NMR (500 MHz, CDC13) d ppm 8.48 (s, 1H); 6.71(s, 1H); 3.78 (s, 3 H); 3.38 (s, 3 H).
2.0 g With triethylamine In dichloromethane at 0 - 20℃; for 15.1667h;
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