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Method for synthesizing alpha-fluorinated thioacrylamide derivative

A technology for substituting acrylamide and trifluoroacrylamide, which is applied in the field of preparation of α-fluorinated thioacrylamide derivatives, can solve the problems of practicality and applicability limitations, harsh reaction conditions, and difficult preparation of raw materials, etc. Healthy operators, easy operation and excellent productivity

Active Publication Date: 2021-02-09
WENZHOU UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the practicability and applicability of these methods are limited due to harsh reaction conditions, unfriendly environment, or difficult preparation of raw materials.

Method used

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  • Method for synthesizing alpha-fluorinated thioacrylamide derivative
  • Method for synthesizing alpha-fluorinated thioacrylamide derivative
  • Method for synthesizing alpha-fluorinated thioacrylamide derivative

Examples

Experimental program
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specific Embodiment 1

[0025] Specific embodiment one: with 20.3 milligrams (0.1mmol) 3,3,3-trifluoro-N-phenylpropanamide, 12.3 milligrams (0.05mmol) 4,4'-dimethyl diphenyl disulfide, 1.9 milligrams ( 0.01mmol) cuprous iodide, 55.3mg (0.4mmol) potassium carbonate, 15.7mg (0.06mmol) triphenylphosphine, 9.0mg (0.5mmol) water were added to 2ml solvent tetrahydrofuran. The reaction was stirred at 80°C for 12 hours. Cool after the reaction, filter the reaction solution to obtain the filtrate, and use a rotary evaporator to remove the solvent to obtain the residue, and the residue is rinsed with an eluent prepared with petroleum ether and ethyl acetate at a volume ratio of 10:1 through a silica gel column. Wash, collect the effluent according to the actual gradient, detect by TLC, combine the effluent containing the target product, use a rotary evaporator to remove the solvent from the combined effluent, and dry in vacuo to obtain a yellow solid 3-fluoro-N-phenyl-3 -(p-tolyl)acrylamide 23.8 mg, yield 83%...

specific Embodiment 2

[0026]Specific example two: 20.3 mg (0.1 mmol) 3,3,3-trifluoro-N-phenylpropanamide, 10.9 mg (0.05 mmol) diphenyl disulfide, 1.9 mg (0.01 mmol) cuprous iodide, 55.3 mg (0.4 mmol) of potassium carbonate, 15.7 mg (0.06 mmol) of triphenylphosphine, and 9.0 mg (0.5 mmol) of water were added to 2 ml of solvent tetrahydrofuran. The reaction was stirred at 80°C for 12 hours. Cool after the reaction, filter the reaction solution to obtain the filtrate, and use a rotary evaporator to remove the solvent to obtain the residue. The residue is rinsed with an eluent prepared with petroleum ether and ethyl acetate at a volume ratio of 10:1 through a silica gel column. Wash, collect the effluent according to the actual gradient, detect by TLC, combine the effluent containing the target product, use a rotary evaporator to remove the solvent from the combined effluent, and dry in vacuo to obtain a yellow solid 3-fluoro-N-phenyl-3 -(phenylthio)acrylamide 20.7 mg, yield 76%. 1H NMR (400MHz, CDCl...

specific Embodiment 3

[0027] Specific example three: 20.3 mg (0.1 mmol) 3,3,3-trifluoro-N-phenylpropanamide, 13.9 mg (0.05 mmol) 4,4'-dimethoxydiphenyl disulfide, 1.9 mg (0.01 mmol) cuprous iodide, 55.3 mg (0.4 mmol) potassium carbonate, 15.7 mg (0.06 mmol) triphenylphosphine, 9.0 mg (0.5 mmol) water were added to 2 ml solvent tetrahydrofuran. The reaction was stirred at 80°C for 12 hours. Cool after the reaction, filter the reaction solution to obtain the filtrate, and use a rotary evaporator to remove the solvent to obtain the residue. The residue is rinsed with an eluent prepared with petroleum ether and ethyl acetate at a volume ratio of 10:1 through a silica gel column. Wash, collect the effluent according to the actual gradient, detect by TLC, combine the effluent containing the target product, remove the solvent by rotating the combined effluent with a rotary evaporator, and dry in vacuo to obtain a yellow solid 3-fluoro-3-((4- Methoxyphenyl)thio)-N-phenylacrylamide 19.7 mg, yield 65%. 1H ...

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Abstract

The invention relates to a method for synthesizing an alpha-fluorinated thioacrylamide derivative. The method comprises the following steps that: with trifluoroacrylamide taken as a reaction substrate, disulfide as a sulfur source, cuprous iodide as a catalyst, potassium carbonate as alkali, triphenylphosphine and water as additives and tetrahydrofuran as a solvent, the components are stirred andreact with one another for 12 hours at 80 DEG C; and after the reaction is finished, a reaction liquid is filtered, a solvent is removed from filtrate by using a rotary evaporator, so that residues can be obtained, column chromatography separation is carried out on the residues by using a silica gel column, leaching is performed with eluent, effluent containing a target product is collected, the effluent is merged, a solvent is removed through vacuum concentration, so that the target product is obtained. The method has the advantages of simple and easily available raw materials, relatively mild reaction conditions, novel and simple preparation process, less pollution and low energy consumption.

Description

technical field [0001] The present invention relates to a preparation method of α-fluorinated thioacrylamide derivatives. Background technique [0002] As an important water-soluble vinyl monomer, α-fluorinated thioacrylamide derivatives are widely used in cosmetics and dye manufacturing, textile industry and water treatment (Neural. Regen. Res. 2021, 16, 150–157; Spectrochim.Acta A 2020,242,118785; Analyst 2002,127,1484–1491; Artif.Organs2003,27,412–418), and it is also an important intermediate for the synthesis of oxindole building blocks (Org.Lett.2014,16, 4594–4597; Chem.Commun.2014, 50, 936–938; Org.Lett.2014, 16, 504–507; J.Am.Chem.Soc.2012, 134, 878–881; Org.Lett.2019, 21, 762–766; Org.Lett. Lett. 2019, 21, 1237–1240). Despite the antifungal and insect toxicity of α-fluorinated thioacrylamides (Chem.Pharm.Bull.1989,37,1932–1933), their synthesis methods are rarely reported (Angew.Chem.Int.Ed.2019, 58, 3533–3537; Angew. Chem. Int. Ed. 2020, 59, 3609–3617). Therefo...

Claims

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Application Information

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IPC IPC(8): C07C323/60C07C319/14C07D333/34C07D213/70C07D277/82
CPCC07C319/14C07D333/34C07D213/70C07D277/82C07C323/60
Inventor 张兴国沈晓钦范东风张小红
Owner WENZHOU UNIVERSITY
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