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Chemical Structure| 363-58-6 Chemical Structure| 363-58-6

Structure of 363-58-6

Chemical Structure| 363-58-6

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Product Details of [ 363-58-6 ]

CAS No. :363-58-6
Formula : C6H6ClF3O3
M.W : 218.56
SMILES Code : O=C(OCC)C(Cl)C(C(F)(F)F)=O
MDL No. :MFCD00041540
InChI Key :YVWUNJVPOCYLIM-UHFFFAOYSA-N
Pubchem ID :2737165

Safety of [ 363-58-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P301+P330+P331-P302+P352-P304+P340-P305+P351+P338-P310
Class:8
UN#:1760
Packing Group:

Application In Synthesis of [ 363-58-6 ]

* 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 [ 363-58-6 ]

[ 363-58-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 363-58-6 ]
  • [ 421-52-3 ]
  • ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In water; ethyl acetate; acetonitrile; Step 3 - Preparation of ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate: To a 3L 4-neck RBF equipped with a mechanical stirrer, reflux condenser, thermometer and addition funnel was charged 358 g of ethyl chlorotrifluoroacetoacetate (1.64 moles), 2,2,2-<strong>[421-52-3]trifluorothioacetamide</strong> and 1000 mL of acetonitrile. To this mixture was added 331.9 g of triethylamine (2.0 eq, 3.28 moles) dropwise over 2.5 hours. During the addition the temperature was maintained at 30-38 C and upon completion of the addition the reaction was heated to reflux for 2 hours and stirred overnight at room temperature. The reaction mixture was filtered and the resulting filtrate was concentrated by rotary evaporation to provide an oily solid which was dissolved in 1500 mL of ethyl acetate. This was washed with 2 x 500 mL of water, 1 x 500 mL of brine and concentrated by rotary evaporation to yield 356.6 g of ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate which was purified by distillation.
  • 2
  • [ 363-58-6 ]
  • [ 89226-13-1 ]
  • [ 232281-06-0 ]
YieldReaction ConditionsOperation in experiment
24.5% N-BOC-Glycine [sic] thioamide (5.0 g, 26.28 mmol) was dissolved in acetonitrile (60 ml), and a solution of ethyl 2-chloro-4,4,4-trifluoroacetoacetate (6.38 g, 26.28 mmol) was added dropwise at 5-10 C. Then, the mixture was stirred for a further 30 minutes at 5 C. and for 12 hours at room temperature. The batch was then cooled to 0 C., and triethylamine (12 ml, 86.77 mmol) was added dropwise. After the mixture had been stirred for 20 minutes at 0 C., the yellow suspension had changed into a clear reddish-brown solution. Then, thionyl chloride (2.1 ml, 28.89 mmol) was slowly added dropwise at 0 C. After the mixture had been stirred for 20 minutes at 0 C., it was warmed to room temperature for a further hour. The solvent was removed on a rotary evaporator, and the residue was taken up in water (100 ml) and extracted repeatedly with ethyl acetate. The combined organic phases were dried (Na2AO4) and concentrated. The crude product was purified by chromatography (silica gel MeOH:DCM=2:98). Yield: 2.2 g (6.4 mmol, 24.5%)
  • 3
  • [ 363-58-6 ]
  • [ 421-52-3 ]
  • ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate [ No CAS ]
  • 2,4-bis-trifluoromethylthiazole-5-carboxvlic acid chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In acetonitrile; Step 3 - Preparation of ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate: To a 3L 4-neck RBF equipped with a mechanical stirrer, reflux condenser, thermometer and addition funnel was charged 358 g of ethyl chlorotrifluoroacetoacetate (1.64 moles), 2,2,2-<strong>[421-52-3]trifluorothioacetamide</strong> and 1000 mL of acetonitrile. To this mixture was added 331.9 g of triethylamine (2.0 eq, 3.28 moles) dropwise over 2.5 hours. During the addition the temperature wasmaintained at 30-38 C and upon completion of the addition the reaction was heated to reflux for 2 hours and stirred overnight at room temperature. The reaction mixture was filtered and the resulting filtrate was concentrated by rotary evaporation to provide an oily solid which was dissolved in 1500 mL of ethyl acetate. This was washed with 2 x 500 mL of water, 1 x 500 mL of brine and concentrated by rotary evaporation to yield 356.6 g of ethyl 2,4-bis-trifluoromethyl-5-thiazole carboxylate which was purified by distillation.
  • 4
  • [ 363-58-6 ]
  • [ 62-55-5 ]
  • [ 117724-63-7 ]
YieldReaction ConditionsOperation in experiment
75.4% With hydrogenchloride; sodium hydroxide; triethylamine; In water; acetonitrile; Example 2 Preparation of 2-Methyl-4-(trifluoromethyl)thiazole-5-carboxylic acid. The reaction of Example 1 may be carried out as generally described and the ester may be converted to the acid by conventional methods without isolation. The following is an example of one method. To a 22 L flask fitted with a mechanical stirrer, thermocouple, and a reflux condenser, was charged thioacetamide (500.6 g, 6.66 mol) and acetonitrile (4 L). This resulted in an endothermic dissolution. To this solution was added ethyl 2-chloro-4,4,4-trifluoroacetoacetate (1105 g, 5.06 mol) over a period of 40 minutes. A slight exotherm occurred which raised the temperature to 55.8 C. The reaction mixture was stirred for 2.3 hours at room temperature during which time a yellow solid precipitated. Then triethylamine (1380 g, 13.64 mol) was added slowly. The reaction temperature rose to about 52 C. The contents were gently refluxed for one hour (internal temperature 75.8 C). After cooling to 46 C, a 40% sodium hydroxide solution (prepared from 1304 g 50% NaOH and 326 mL water, 16.3 mol) was added over 10 minutes. An exotherm to 53.6 C was noted. The mixture was placed under a vacuum of 95 mm and the solvent distilled from the reaction until only water (of saponification) is present in the distillate. To the remaining reaction mixture was added 2 L water and 1.5 kg ice. Then concentrated HCl (1500 mL, 18 mol) was added over a 15 minute period to bring the pH to less than 2. Another 2 L water and 2 kg ice were added, and the product was filtered, washed on the filter with 12 L water, and dried in a vacuum oven to obtain 2-methyl-4-(trifluoromethyl)thiazole-5-carboxylic acid, 825 g as a beige solid, a 75.4% yield at 97.6% purity.
  • 6
  • [ 363-58-6 ]
  • [ 42182-27-4 ]
  • ethyl 7-cyano-2-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% In ethanol;Reflux; Step 1 [0413] 2-Amino-4-cyanopyridine (1.00 g, 8.39 mmol) was dissolved in ethanol (5.0 mL), ethyl 2-chloro-4,4,4-trifluoroacetoacetate (2.52 g, 9.23 mmol) was added thereto, and the mixture was stirred under reflux with heating overnight. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate = 80/20), and then reslurried in tert-butyl methyl ether, whereby ethyl 7-cyano-2-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate (1.11 g, yield 47percent) was obtained. 1H NMR (300 MHz, CDCl3, delta): 9.55 (dd, J = 7.1, 0.9 Hz, 1H), 8.20 (dd, J = 1.1, 0.9 Hz, 1H), 7.30 (dd, J = 7.3, 1.1 Hz, 1H), 4.51 (q, J = 7.1 Hz, 2H), 1.45 (t, J = 7.1 Hz, 3H); ESIMS m/z: [M + H]+ 284.
 

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Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Ester Cleavage • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Heat of Combustion • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions with Organometallic Reagents • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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