CN101407484A - Method for synthesizing beta-carbonyl thioacid amide compound - Google Patents
Method for synthesizing beta-carbonyl thioacid amide compound Download PDFInfo
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- CN101407484A CN101407484A CNA2008100514550A CN200810051455A CN101407484A CN 101407484 A CN101407484 A CN 101407484A CN A2008100514550 A CNA2008100514550 A CN A2008100514550A CN 200810051455 A CN200810051455 A CN 200810051455A CN 101407484 A CN101407484 A CN 101407484A
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Abstract
The invention provides a method for synthesizing a beta-carbonyl thioamide compound, particularly relating to a method for synthesizing a beta-carbonyl thioamide compound through one step by a 1, 3-dicarbonyl compound and sulfo-isocyanate. The invention solves problems of existing thioamide compound synthesizing method of poor generative selectivity, strict reaction condition and low yield coefficient. The method for synthesizing the beta-carbonyl thioamide compound has good selectivity, moderate reaction condition and yield coefficient between 70-95 percent.
Description
Technical field
The invention belongs to a kind of synthetic method of β-beta-carbonyl thioacid amide compound, particularly a kind of by 1, the synthetic method of 3-dicarbonyl compound and isothiocyanic acid ester one-step synthesis β-beta-carbonyl thioacid amide compound.
Background technology
Thioamide analog compound is the important carboxylic acid derivative of a class, has important biology, pharmaceutical activity; As the multi-functional organic synthesis intermediate of a class, obtained to use widely simultaneously in fields such as Synthetic Organic Chemistry, medicine synthetic chemistry, materials chemistries.From present existing document, adopting amides to carry out sulfo-by thiophosphoric anhydride or Lawson (Lawesson) reagent is the most frequently used a kind of synthetic method (Chem.Rev. of thioamide analog compound, 1961,45), adopting fragrance or heteroaromatic compound and isothiocyanic acid ester synthetic thioamide analog compound under Louis (Lewis) acid effect is the novel method (Synthesis that recent two decades development, 1988,717; Tetrahedron, 1986,42,3683).Yet there are shortcomings such as raw material sources are limited, product generation poor selectivity, association by product, severe reaction conditions in existing synthetic method more.Therefore, the acquisition of the exploitation of the novel method for synthesizing of thioamide analog compound and novel thioamide analog compound is organic chemistry and pharmaceutical chemical hot research field always.
Summary of the invention
The objective of the invention is provides a kind of novel method for synthesizing of β-beta-carbonyl thioacid amide compound at generating problems such as poor selectivity, severe reaction conditions, productive rate be low in the existing thioamide analog compound synthetic method.
The structural formula II I of β-beta-carbonyl thioacid amide compound provided by the present invention is expressed as follows:
Wherein, R
1Be PhNH, 4-MePhNH-, 4-MeOPhNH-, 4-EtOPhNH-, 4-ClPhNH-, 4-BrPhNH-, 4-FPhNH-, 4-NO
2PhNH-, 4-CNPhNH-, 3-MePhNH-, 3-MeOPhNH-, 3-EtOPhNH-, 3-ClPhNH-, 3-BrPhNH-, 3-FPhNH-, 3-NO
2PhNH-, 2-MePhNH-, 2-MeOPhNH-, 2-ClPhNH-, 2-BrPhNH, 2-FPhNH-, 2-CNPhNH-, 3-ClPhNH-, 2,4-Me
2PhNH-, 3,4-Me
2PhNH-, 3,5-Me
2PhNH-, 3,4,5-Me
3PhNH-, 2,5-(MeO)
2PhNH-, 2,4-(MeO)
2PhNH-, 3,5-(MeO)
2PhNH-, 3,4,5-(MeO)
3PhNH-, 2-MeO-5-ClPhNH-, 2,5-(MeO)
2-4-ClPhNH-, NH
2, NHMe, NHEt, PhCH
2NH-, NMe
2, Me-, MeO-, EtO-, PhCH
2O-, PhO-, Ph-, 4-MePh-, 4-EtOPh-, 4-MeOPh-4-ClPh-, 4-BrPh-, 4-FPh-, 4-NO
2Ph-, 4-CNPh-, 2-MePh-, 2-MeOPh-, 2-ClPh-, 2-BrPh-or 2-FPh-;
R
2Be Me-, Et-, PhCH
2-, Ph-, 4-MePh-, 4-MeOPh-, 4-EtOPh-, 4-ClPh-, 4-BrPhNH-, 4-FPh-, 4-NO
2Ph-, 4-CNPh-, 3-MePh-, 3-MeOPh-, 3-EtOPh-, 3-ClPh-, 3-BrPhNH-, 3-FPh-, 2-MePh-, 2-MeOPh-, 2-ClPh-, 2-BrPh, 2-FPh-, 2-CNPh-, 3-ClPh-, 3-NO
2Ph-, 2,4-Me
2Ph-, 3,4-Me
2Ph-, 3,5-Me
2Ph-, 3,4,5-Me
3Ph-, 2,5-(MeO)
2Ph-, 2,4-(MeO)
2Ph-, 3,5-(MeO)
2Ph-, 3,4,5-(MeO)
3Ph-, 2-MeO-5-ClPh-or 2,5-(MeO)
2-4-ClPh-;
The preparation method's of β involved in the present invention-beta-carbonyl thioacid amide compound III step and condition are as follows:
β provided by the present invention-beta-carbonyl thioacid amide compound III, by 1,3-dicarbonyl compound I and isothiocyanic acid ester II are synthetic under alkaline condition, and reaction equation is as follows:
Wherein, used alkali is in the reaction: K
2CO
3Or Na
2CO
3Solvent for use is in the reaction: ethanol, methyl alcohol, N, dinethylformamide, N,N-dimethylacetamide or dimethyl sulfoxide (DMSO);
Preparation method's step and condition are as follows: to reflux condensing tube is housed, press in the reactor of agitator (10～100): 1.0: (1.0～1.2): (1.0～1.2) mol ratio adds solvent successively, 1,3-dicarbonyl compound I, isothiocyanic acid ester II and alkali, stirred under the reaction mixture room temperature 0.5～1.0 hour, be warming up to 50～100 ℃ afterwards, continue to stir 1.0～10.0 hours, stopped reaction, steam and remove reaction solvent, system is cooled to room temperature, in reactor, add dilute hydrochloric acid and be neutralized to neutrality, solid is separated out, and the gained throw out is filtered, washing, vacuum-drying obtains thioamide analog compound III.
Beneficial effect: the invention solves and generate problems such as poor selectivity, severe reaction conditions, productive rate are low in the existing thioamide analog compound synthetic method, selectivity of the present invention is good, the reaction conditions gentleness, and productive rate is between 70～95%.
Embodiment
Embodiment 1
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add ethanol (15 milliliters), N-phenyl aceto-acetamide (5.0 mmole), salt of wormwood (6.0 mmole) and thiocarbanil (6.0 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to backflow, after stirring 1.5 hours under this temperature, stopped reaction, normal pressure steams and removes ethanol, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 94%.Reaction equation is expressed as follows:
Embodiment 2
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add methyl alcohol (15 milliliters), N-(2-aminomethyl phenyl) aceto-acetamide (5.0 mmole), yellow soda ash (6.0 mmole) and thiocarbanil (6.0 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to backflow, after stirring 1.5 hours under this temperature, stopped reaction, normal pressure steams and removes ethanol, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 93%.Reaction equation is expressed as follows:
Embodiment 3
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add ethanol (20 milliliters), N-(2-p-methoxy-phenyl) aceto-acetamide (5.0 mmole), salt of wormwood (5.5 mmole) and thiocarbanil (5.5 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to backflow, after stirring 1.6 hours under this temperature, stopped reaction, normal pressure steams and removes ethanol, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 93%.Reaction equation is expressed as follows:
Embodiment 4
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add methyl alcohol (15 milliliters), N-(4-chloro-phenyl-) aceto-acetamide (5.0 mmole), salt of wormwood (6.0 mmole) and thiocarbanil (6.0 mmole), stir after 0.5 hour under the room temperature, with 50 ℃ of reaction system heating, after stirring 1.7 hours under this temperature, stopped reaction, normal pressure steams and removes methyl alcohol, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 96%.Reaction equation is expressed as follows:
Embodiment 5
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add N, dinethylformamide (20 milliliters), N-(4-p-methoxy-phenyl) aceto-acetamide (5.0 mmole), salt of wormwood (5.5 mmole) and thiocarbanil (5.5 mmole), stir after 0.5 hour under the room temperature, with 100 ℃ of reaction system heating, after stirring 1.8 hours under this temperature, stopped reaction removes N under reduced pressure, dinethylformamide, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 93%.Reaction equation is expressed as follows:
Embodiment 6
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add ethanol (15 milliliters), N-(4-aminomethyl phenyl) aceto-acetamide (5.0 mmole), yellow soda ash (6.0 mmole) and thiocarbanil (6.0 mmole), stir after 0.5 hour under the room temperature, with 60 ℃ of reaction system heating, after stirring 1.5 hours under this temperature, stopped reaction, normal pressure steams and removes ethanol, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 92%.Reaction equation is expressed as follows:
Embodiment 7
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add methyl alcohol (20 milliliters), N-(2-chloro-phenyl-) aceto-acetamide (5.0 mmole), yellow soda ash (6.0 mmole) and thiocarbanil (6.0 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to reflux state, after stirring 1.6 hours under this temperature, stopped reaction, normal pressure steams and removes methyl alcohol, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 94%.Reaction equation is expressed as follows:
Embodiment 8
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add methyl alcohol (15 milliliters), N-(2, the 4-3,5-dimethylphenyl) aceto-acetamide (5.0 mmole), salt of wormwood (5.5 mmole) and thiocarbanil (5.5 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to reflux state, after stirring 1.7 hours under this temperature, stopped reaction, normal pressure steam and remove methyl alcohol, and system naturally cools to room temperature, in reaction flask, add dilute hydrochloric acid (10%, 15 milliliters), stir, the gained throw out is filtered, washing, vacuum-drying, get the thioamide analog product, productive rate 94%.Reaction equation is expressed as follows:
Embodiment 9
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add N, N-N,N-DIMETHYLACETAMIDE (20 milliliters), N-(2-methyl-4-chloro-phenyl-) aceto-acetamide (5.0 mmole), salt of wormwood (6.0 mmole) and thiocarbanil (6.0 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to 100 ℃, after stirring 1.8 hours under this temperature, stopped reaction removes N under reduced pressure, the N-N,N-DIMETHYLACETAMIDE, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 89%.Reaction equation is expressed as follows:
Embodiment 10
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add N, dinethylformamide (15 milliliters), N-(4-chloro-phenyl-) aceto-acetamide (5.0 mmole), salt of wormwood (6.0 mmole) and ethyl mustard oil (6.0 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to 80 ℃, under this temperature, continue to stir 1.0 hours, stopped reaction removes reaction solvent under reduced pressure, and system naturally cools to room temperature, in reaction flask, add dilute hydrochloric acid (10%, 15 milliliters), and stir, the gained throw out is filtered, washing, vacuum-drying, get the thioamides product, productive rate 87%.Reaction equation is expressed as follows:
Embodiment 11
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add ethanol (10 milliliters), water (5 milliliters), N-(4-aminomethyl phenyl) aceto-acetamide (5.0 mmole), salt of wormwood (5.5 mmole) and benzyl isothiocyanide (5.5 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to reflux state, after stirring 2.2 hours under this temperature, stopped reaction, normal pressure steams and removes ethanol, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 81%.Reaction equation is expressed as follows:
Embodiment 12
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add ethanol (15 milliliters), N-methyl aceto-acetamide (5.0 mmole), salt of wormwood (6.0 mmole) and thiocarbanil (6.0 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to reflux state, after stirring 4.0 hours under this temperature, stopped reaction, normal pressure steams and removes ethanol, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 80%.Reaction equation is expressed as follows:
Embodiment 13
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add ethanol (7 milliliters), water (7 milliliters), N-phenyl aceto-acetamide (5.0 mmole), salt of wormwood (6.0 mmole) and thiocarbanil (6.0 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to backflow, after stirring 1.5 hours under this temperature, stopped reaction, normal pressure steams and removes ethanol, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 94%.Reaction equation is expressed as follows:
Embodiment 14
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add ethanol (20 milliliters), N-phenyl aceto-acetamide (5.0 mmole), salt of wormwood (6.0 mmole) and benzyl isothiocyanide (6.0 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to reflux state, after stirring 2.0 hours under this temperature, stopped reaction, normal pressure steams and removes ethanol, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 83%.Reaction equation is expressed as follows:
Embodiment 15
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add ethanol (15 milliliters), N-(4-aminomethyl phenyl) aceto-acetamide (5.0 mmole), salt of wormwood (5.5 mmole) and benzyl isothiocyanide (5.5 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to reflux state, after stirring 2.2 hours under this temperature, stopped reaction, normal pressure steams and removes ethanol, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 81%.Reaction equation is expressed as follows:
Embodiment 16
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add N, dinethylformamide (20 milliliters), N-(4-chloro-phenyl-) aceto-acetamide (5.0 mmole), salt of wormwood (5.5 mmole) and benzyl isothiocyanide (5.5 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to 100 ℃, after stirring 2.1 hours under this temperature, stopped reaction removes N under reduced pressure, dinethylformamide, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 77%.Reaction equation is expressed as follows:
Embodiment 17
Reflux condensing tube is being housed, in 50 milliliters of round-bottomed flasks of agitator, add methyl-sulphoxide (15 milliliters), N-(4-p-methoxy-phenyl) aceto-acetamide (5.0 mmole), salt of wormwood (6.0 mmole) and benzyl isothiocyanide (5.5 mmole), stir after 0.5 hour under the room temperature, reaction system is heated to 100 ℃, after stirring 1.8 hours under this temperature, stopped reaction, remove methyl-sulphoxide under reduced pressure, system naturally cools to room temperature, adds dilute hydrochloric acid (10%, 15 milliliter) in reaction flask, stir, the gained throw out is filtered, washing, vacuum-drying gets the thioamide analog product, productive rate 78%.Reaction equation is expressed as follows:
Claims (1)
1, a kind of synthetic method of β-beta-carbonyl thioacid amide compound is characterized in that, step and condition are as follows:
The structural formula II I of described β-beta-carbonyl thioacid amide compound is expressed as follows:
In the formula, R
1Be PhNH, 4-MePhNH-, 4-MeOPhNH-, 4-EtOPhNH-, 4-ClPhNH-, 4-BrPhNH-, 4-FPhNH-, 4-NO
2PhNH-, 4-CNPhNH-, 3-MePhNH-, 3-MeOPhNH-, 3-EtOPhNH-, 3-ClPhNH-, 3-BrPhNH-, 3-FPhNH-, 3-NO
2PhNH-, 2-MePhNH-, 2-MeOPhNH-, 2-ClPhNH-, 2-BrPhNH, 2-FPhNH-, 2-CNPhNH-, 3-ClPhNH-, 2,4-Me
2PhNH-, 3,4-Me
2PhNH-, 3,5-Me
2PhNH-, 3,4,5-Me
3PhNH-, 2,5-(MeO)
2PhNH-, 2,4-(MeO)
2PhNH-, 3,5-(MeO)
2PhNH-, 3,4,5-(MeO)
3PhNH-, 2-MeO-5-ClPhNH-, 2,5-(MeO)
2-4-ClPhNH-, NH
2, NHMe, NHEt, PhCH
2NH-, NMe
2, Me-, MeO-, EtO-, PhCH
2O-, PhO-, Ph-, 4-MePh-, 4-EtOPh-, 4-MeOPh-4-ClPh-, 4-BrPh-, 4-FPh-, 4-NO
2Ph-, 4-CNPh-, 2-MePh-, 2-MeOPh-, 2-ClPh-, 2-BrPh-or 2-FPh-;
R
2Be Me-, Et-, PhCH
2-, Ph-, 4-MePh-, 4-MeOPh-, 4-EtOPh-, 4-ClPh-, 4-BrPhNH-, 4-FPh-, 4-NO
2Ph-, 4-CNPh-, 3-MePh-, 3-MeOPh-, 3-EtOPh-, 3-ClPh-, 3-BrPhNH-, 3-FPh-, 2-MePh-, 2-MeOPh-, 2-ClPh-, 2-BrPh, 2-FPh-, 2-CNPh-, 3-ClPh-, 3-NO
2Ph-, 2,4-Me
2Ph-, 3,4-Me
2Ph-, 3,5-Me
2Ph-, 3,4,5-Me
3Ph-, 2,5-(MeO)
2Ph-, 2,4-(MeO)
2Ph-, 3,5-(MeO)
2Ph-, 3,4,5-(MeO)
3Ph-, 2-MeO-5-ClPh-or 2,5-(MeO)
2-4-ClPh-;
Described β-beta-carbonyl thioacid amide compound III, by 1,3-dicarbonyl compound I and isothiocyanic acid ester II are synthetic under alkaline condition, and reaction equation is as follows:
Wherein, used alkali is in the reaction: K
2CO
3Or Na
2CO
3Solvent for use is in the reaction: ethanol, methyl alcohol, N, dinethylformamide, N,N-dimethylacetamide or dimethyl sulfoxide (DMSO);
To reflux condensing tube is housed, press in the reactor of agitator (10～100): 1.0: (1.0～1.2): (1.0～1.2) molar ratio adds solvent successively, 1,3-dicarbonyl compound I, isothiocyanic acid ester II and alkali, stirred under the reaction mixture room temperature 0.5～1.0 hour, be warming up to 50～100 ℃ afterwards, continue to stir 1.0～10.0 hours, stopped reaction, steam and remove reaction solvent, system is cooled to room temperature, add dilute hydrochloric acid in the reactor and be neutralized to neutrality, solid is separated out, and the gained throw out is filtered, washing, vacuum-drying obtains a kind of β-beta-carbonyl thioacid amide compound.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109675723A (en) * | 2019-01-29 | 2019-04-26 | 中南大学 | Collecting agent and its preparation method and application with amide groups and thioamides base |
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2008
- 2008-11-24 CN CNA2008100514550A patent/CN101407484A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109675723A (en) * | 2019-01-29 | 2019-04-26 | 中南大学 | Collecting agent and its preparation method and application with amide groups and thioamides base |
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Open date: 20090415 |