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Chemical Structure| 220239-64-5 Chemical Structure| 220239-64-5

Structure of 220239-64-5

Chemical Structure| 220239-64-5

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Product Details of [ 220239-64-5 ]

CAS No. :220239-64-5
Formula : C6H2ClF3O2S
M.W : 230.59
SMILES Code : O=S(C1=C(F)C=C(F)C=C1F)(Cl)=O
MDL No. :MFCD01091015
InChI Key :XINCBNCLCIQIJM-UHFFFAOYSA-N
Pubchem ID :2776983

Safety of [ 220239-64-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 220239-64-5 ]

* 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 [ 220239-64-5 ]

[ 220239-64-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1235406-42-4 ]
  • [ 220239-64-5 ]
  • [ 1450598-74-9 ]
YieldReaction ConditionsOperation in experiment
58% To a solution of <strong>[1235406-42-4]tert-butyl thiazol-4-ylcarbamate</strong> (140.0 g, 699.1 mmol) in anhydrous tetrahydrofuran (700 mL) was added a 1 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (758.9 mL, 758.0 mmol) at -78 C. The reaction mixture was allowed to warm to 0 C. and stirred for 20 minutes. After cooling the reaction mixture to -78 C., a solution of 2,4,6-trifluorobenzenesulfonyl chloride (175.0 g, 758.9 mmol) in anhydrous tetrahydrofuran (200 mL) was added slowly to it. The reaction mixture was allowed to warm to ambient temperature, stirred for 12 h, and then quenched by addition of saturated ammonium chloride (200 mL). The mixture was extracted with ethyl acetate (3×1000 mL). The organic phase was washed with brine (3×1000 mL), dried over anhydrous sodium sulfate, and filtered. Concentration in vacuo and trituration of the residue in methanol (100 mL) provided the title compound as a colorless solid (140.0 g, 58% yield): 1H NMR (400 MHz, CDCl3) delta8.81 (d, J=2.1 Hz, 1H), 7.53 (d, J=2.1 Hz, 1H), 6.85 (br t, J=8.4 Hz, 2H), 1.39 (s, 9H); MS (ES+) m/z 417.0 (M+23).
58% To a solution of terf-butyl thiazol-4-ylcarbamate (140.0 g, 699.1 mmol) in anhydrous tetrahydrofuran (700 ml_) was added a 1 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (758.9 ml_, 758.9 mmol) at -78 C. The reaction mixture was allowed to warm to 0 C and stirred for 20 minutes. After cooling the reaction mixture to -78 C, a solution of 2,4,6-trifluorobenzenesulfonyl chloride (175.0 g, 758.9 mmol) in anhydrous tetrahydrofuran (200 ml_) was slowly added to it. The reaction mixture was allowed to warm to ambient temperature, stirred for 12 h, and then quenched by addition of saturated aqueous ammonium chloride (200 ml_). The mixture was extracted with ethyl acetate (3 c 1000 ml_). The organic phase was washed with brine (3 c 1000 ml_), dried over anhydrous sodium sulfate, and filtered. Concentration in vacuo and trituration of the residue in methanol (100 ml_) provided the title compound as a colorless solid (140.0 g, 58% yield): 1H NMR (400 MHz, CDCI3) d 8.81 (d, J = 2.1 Hz, 1 H), 7.53 (d, J = 2.1 Hz, 1 H), 6.85 (br t, J = 8.4 Hz, 2H), 1.39 (s, 9H); MS (ES+) m/z 417.0 (M + 23).
47% EXAMPLE 286 Synthesis of (S)-4-((1-benzylpyrrolidin-3-yl)(methyl)amino)-2,6-difluoro-//-(thiazol-4- yl)benzenesulfonamide formate Step 1. Preparation of te/f-butyl thiazol-4-yl((2,4,6-trifluorophenyl)sulfonyl)carbamate To a solution of terf-butyl thiazol-4-ylcarbamate (0.96 g, 4.8 mmol) in anhydrous tetrahydrofuran (20 mL) was added a 1 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (5.76 mL, 5.76 mmol) at -78 C. The reaction mixture was allowed to warm to ambient temperature and stirred for 1 h. The reaction mixture was cooled to - 78 C, and a solution of 2,4,6-trifluorobenzenesulfonyl chloride (1.32 g, 5.76 mmol) in anhydrous tetrahydrofuran (10 mL) was added to it. The reaction mixture was allowed to warm to ambient temperature and stirred for 3 h. The mixture was diluted with ethyl acetate (35 mL), washed with saturated ammonium chloride (2 chi 30 mL), brine (2 chi 30 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo and purification of the residue by column chromatography, eluting with a gradient of 0 to 50% of ethyl acetate in hexanes, provided the title compound as a colorless solid (0.67 g, 47% yield): MS (ES+) m/z 395.0 (M + 1).
 

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• Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • 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 Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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