CN106831285B - Method for converting amide and urea into ester - Google Patents
Method for converting amide and urea into ester Download PDFInfo
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- CN106831285B CN106831285B CN201710133702.0A CN201710133702A CN106831285B CN 106831285 B CN106831285 B CN 106831285B CN 201710133702 A CN201710133702 A CN 201710133702A CN 106831285 B CN106831285 B CN 106831285B
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/12—Formation or introduction of functional groups containing oxygen of carboxylic acid ester groups
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
- C07C67/20—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from amides or lactams
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
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Abstract
The invention provides a method for converting amide and urea into ester, which takes different amide and urea as substrates, alcohol or phenol as a nucleophilic reagent, ferric salt as a catalyst and acid as an additive to realize the conversion of the amide and the urea into the ester under mild conditions. The method is characterized in that the conversion of amide into ester is realized in one step by using cheap and easily available iron salt as a catalyst and commercialized amide, urea and alcohol as substrates. The method has the advantages of mild reaction conditions, cheap and easily-obtained raw materials, wide adaptability of reaction substrates, high selectivity and yield of products, environmental protection and the like, and has good industrial application prospect.
Description
[ technical field ] A method for producing a semiconductor device
The invention relates to the field of organic synthesis, in particular to a method for converting amide and urea into ester.
[ background of the invention ]
Ester molecules are one of the most important and fundamental functional groups in organic chemistry and biochemistry, and have wide applications in fine chemicals, agrochemical chemicals, polymers, and pharmaceuticals. The compound has wide application as solvent, lubricant, pesticide, perfume and medicine, and has wide medicinal value, such as NF-kB inhibitor CAPE and capsaicin, bee propolis contact allergen isopentenyl caffeate, EGCG simulant HIV-1 reverse transcriptase inhibitor hydroxytyrosol gallate, etc. In particular carbonic acid diester compounds, are used as solvents for cellulose nitrate, cellulose ethers, synthetic resins and natural resins in chemical production; in the pharmaceutical industry for the manufacture of phenobarbital; the pesticide industry is used for manufacturing pyrethrum. Therefore, the synthesis of ester compounds is not only a major focus of attention in the pharmaceutical field, but also one of the most important issues in the research of organic synthesis and other industrial fields.
There are many synthetic methods for converting amides or ureas to esters, among which there are three main methods, the first is direct activation of amide bonds with activating reagents, the second is increasing the sensitivity of amides to nucleophiles by destruction of amide resonances; the third is to use a catalyst to activate the amide bond, increasing the ability of the nucleophile to attack the carbonyl. In recent years, synthetic methods for converting amides or ureas into ester compounds have been reported successively: (1) sc (OTf) is reported by Kazushi Mashima topic group3Catalyzing amide and alcohol to react to synthesize ester through C-N bond breaking; (2) kazushi Mashima topic group reported Zn (OTf)2Catalyzing amide and alcohol to react to synthesize ester compound; (3) CeO reported by Kenichi Shimizua topic group2Catalyzing amide and alcohol to react to synthesize ester compound; (4) gaig first reported that Ni catalyzes the reaction of amides with alcohols to synthesize ester compounds by Ni-catalyzed cleavage between C-N in the amide molecule. Although the primary amide-based compounds can be efficiently synthesized by these methods, there are problems such as the use of expensive catalysts, or higher temperatures and lower yields. Therefore, it is one of the problems to be solved by the present invention to develop a method for synthesizing an ester compound with high yield using an inexpensive transition metal as a catalyst. (references: adv. Synth. Catal.,2013,355,3391-)。
The invention provides a method for converting amide and urea into ester with high yield by using iron salt as a catalyst and acid as an additive under mild conditions and with simple operation.
[ summary of the invention ]
The invention aims to develop a method for synthesizing ester with high conversion rate and high yield by using cheap and easily-obtained amide and urea under the catalysis of Fe salt and in a mild environment.
The invention aims to be realized by the following technical scheme:
a synthesis method of an ester (I) compound with the following structural formula comprises the following operation steps: adding amide, urea and alcohol with different structures into a reaction vessel filled with ferric salt, then adding a catalytic amount of acid and a solvent, stirring at a proper reaction temperature, washing with water or a saturated salt solution after the reaction is finished, then extracting with an organic solvent, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product:
r is C2～C8The linear alkyl group of (1), phenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-nitrophenyl group, 4-hydroxyphenyl group, 4-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group, 4-trifluoromethylphenyl group, 4-cyanophenyl group, 3-methylphenyl group, 2-thienyl group, 2-pyridyl group, 1-naphthyl group, 2-naphthyl group, p-phenylphenyl group.
R1Is C2～C8The linear alkyl group, isopropyl group, isopentyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, benzyl group, p-methylbenzyl group, p-bromobenzyl group, naphthylmethyl group, 2-thienylmethyl group, 2-picolyl group, phenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-nitrophenyl group, 4-hydroxyphenyl group, 4-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group, 4-trifluoromethylphenyl group, 4-cyanophenyl group, 3-methylphenyl group, 2-thienyl group, 2-pyridyl group, 1-naphthyl group, 2-naphthyl group, p-phenylphenyl group of (A).
The mol ratio of the amide, the Fe salt and the acid is 1: [0.1-1.0] to [0.1-1.0 ].
The temperature is mainly 25-120 ℃.
The organic solvent is one or more than two selected from N, N-dimethylformamide, N-hexane, cyclohexane, dimethyl sulfoxide, acetonitrile, 1, 4-dioxane, tetrahydrofuran, toluene, N-methylpyrrolidone, chlorobenzene, 1, 2-xylene or 1, 2-dichloroethane.
The catalyst is selected from Fe and Fe2O3、Fe3O4、FeCl2、FeCl3、FeCl3·6H2O、Fe(NO3)3·6H2O、Fe2(SO4)3·H2One or more than two of O.
The acid is one or more than two selected from benzoic acid, phenylacetic acid, benzenesulfonic acid, trifluoroacetic acid, naphthylacetic acid, concentrated hydrochloric acid and concentrated nitric acid.
The amide or urea substrate is selected from benzamide, 4-methylbenzamide, 4-methoxybenzamide, 4-nitrobenzamide, 4-hydroxybenzamide, 4-fluorobenzamide, 4-chlorobenzamide, 4-bromobenzamide, 4-iodobenzamide, 4-trifluoromethylbenzamide, 3-methylbenzamide, 4-cyanobenzamide, 2-thiophenylbenzamide, 2-pyridinebenzamide, 1-naphthalenesenzamide, 2-naphthalenesenzamide, acrylamide, p-phenylbenzamide, propionamide, valeramide, N-dimethylformamide, N-dimethylbenzamide, N-dimethylacetamide and urea.
The alcohol or phenol is selected from C2～C8The alkyl alcohol, isopropanol, isoamyl alcohol, tertiary butyl alcohol, cyclopentanol, cyclohexanol, benzyl alcohol, p-methylbenzyl alcohol, p-bromobenzyl alcohol, naphthalenemethanol, 2-thiophenemethanol, 2-pyridinemethanol, phenol, 4-methylphenol, 4-methoxyphenol, 4-nitrophenol, 4-hydroxyphenol, 4-fluorophenol, 4-chlorophenol, 4-bromophenol, 4-iodophenol, 4-trifluoromethylphenol, 4-cyanophenol, 3-methylphenol.
The synthetic route involved in the invention is as follows:
according to experimental results, the invention provides a method for synthesizing ester by taking Fe salt as a catalyst, acid as an additive and cheap and easily-obtained amide and urea as raw materials. The method has the advantages of simple operation, mild reaction conditions, environmental protection, high selectivity, high yield and the like, and has good industrial application prospect.
[ brief description of the drawings ]
FIG. 1 is a synthetic scheme for converting amide and urea into ester.
[ detailed description ] embodiments
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Synthesis of ester Compound
As shown in fig. 1, the synthesis steps of the ester compound (I) provided by the present invention are:
adding 0.2mmol amide (such as benzamide and the like), 10 mol% -100 mol% acid, 2ml solvent (such as N, N-dimethylformamide) and 0.2mmol alcohol or phenol into a reaction tube filled with 10-100 mol% of iron salt catalyst, reacting at 25-120 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform (or ethyl acetate), drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain the target product:
synthesis example 1
Synthesis of methyl benzoate
Adding 0.2mmol of benzamide, 10 mol% of acetic acid, 2ml of solvent N, N-dimethylformamide and 0.2mmol of methanol into a reaction tube filled with 10 mol% of Fe powder catalyst, reacting at 25 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 70%.
Synthesis example 2
Synthesis of tert-butyl benzoate
At a concentration of 30 mol% Fe2O3Adding 0.2mmol of benzamide, 20 mol% of nitric acid, 2ml of solvent DMSO and 0.2mmol of tert-butyl alcohol into a reaction tube of a catalyst, reacting at 50 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 55%.
Synthesis example 3
Synthesis of cyclohexyl benzoate
In the presence of 50 mol% FeCl3Adding 0.2mmol of benzamide, 50 mol% of benzoic acid, 2ml of solvent acetonitrile and 0.2mmol of cyclohexanol into a reaction tube of a catalyst, reacting at 50 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 61%.
Synthesis example 4
Synthesis of benzyl benzoate
At a concentration of 20 mol% Fe3O4Adding 0.2mmol of benzamide, 30 mol% of trifluoromethanesulfonic acid, 2ml of solvent n-hexane and 0.2mmol of benzyl alcohol into a reaction tube of a catalyst, reacting at 60 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 86%.
Synthesis example 5
Synthesis of phenethyl benzoate
In the presence of 60 mol% FeCl2Adding 0.2mmol of benzamide, 40 mol% of naphthylacetic acid, 2ml of solvent 1, 4-dioxane and 0.2mmol of phenethyl alcohol into a reaction tube of a catalyst, reacting at 50 ℃, and reacting by using a catalyst after the reaction is finishedWashing with water or saturated salt solution, extracting with chloroform, drying, distilling under reduced pressure, concentrating to remove solvent, and separating the crude product by column chromatography to obtain the target product: the yield was 70%.
Synthesis example 6
Synthesis of naphthyl ethyl benzoate
In the presence of 80 mol% FeCl3·6H2Adding 0.2mmol of benzamide, 40 mol% concentrated hydrochloric acid, 2ml of solvent N-methyl pyrrolidone and 0.2mmol of naphthalene methanol into a reaction tube of an O catalyst, reacting at 100 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 45%.
Synthesis example 7
Synthesis of phenyl benzoate
At a concentration of 30 mol% Fe2(SO4)3·H2Adding 0.2mmol of benzamide, 20 mol% of benzoic acid, 2ml of solvent toluene and 0.2mmol of phenol into a reaction tube of an O catalyst, reacting at 70 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 55%.
Synthesis example 8
Synthesis of p-methylphenyl benzoate
At a concentration of 20 mol% Fe2(SO4)3·H2Adding 0.2mmol of benzamide, 20 mol% of phenylacetic acid, 2ml of solvent chlorobenzene and 0.2mmol of p-methylphenol into a reaction tube of an O catalyst, reacting at 90 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 61%.
Synthesis example 9
Synthesis of p-chlorophenyl benzoate
In the presence of 70 mol% Fe (NO)3)3·6H20.2m of O catalyst was added to the reaction tubemol benzamide, 20mol percent trifluoromethanesulfonic acid, 2ml solvent 1, 2-xylene and 0.2mmol p-chlorophenol, reacting at 80 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain the target product: the yield was 71%.
Synthesis example 10
Synthesis of ethyl phenylacetate
Adding 0.2mmol of phenylacetamide, 10 mol% of benzoic acid, 2ml of solvent N, N-dimethylformamide and 0.2mmol of ethanol into a reaction tube filled with 80 mol% of Fe powder catalyst, reacting at 85 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 67%.
Synthesis example 11
Synthesis of ethyl naphthoate
In the presence of 10 mol% FeCl2Adding 0.2mmol of naphthamide, 30 mol% of acetic acid, 2ml of solvent cyclohexane and 0.2mmol of ethanol into a reaction tube of a catalyst, reacting at 100 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 45%.
Synthesis example 12
Synthesis of phenyl 2-picolinate
In the presence of 30 mol% Fe (NO)3)3·6H2Adding 0.2mmol of 2-pyridine formamide, 80 mol% hydrochloric acid, 2ml of solvent tetrahydrofuran and 0.2mmol of phenol into a reaction tube of an O catalyst, reacting at 70 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 57%.
Synthesis example 13
Synthesis of dimethyl carbonate
In the presence of 50 mol% FeCl3In the reaction tube of the catalyst, the catalyst is added,adding 0.2mmol of urea, 30 mol% of phenylacetic acid, 2ml of solvent N, N-dimethylformamide and 0.4mmol of methanol, reacting at 55 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 62%.
Synthesis example 14
Synthesis of diethyl carbonate
Adding 0.2mmol of urea, 20 mol% of naphthylacetic acid, 2ml of 1, 4-dioxane as a solvent and 0.4mmol of ethanol into a reaction tube filled with 80 mol% of Fe powder catalyst, reacting at 90 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 46%.
Synthesis example 15
Synthesis of diphenyl carbonate
In the presence of 40 mol% Fe (NO)3)3·6H2Adding 0.2mmol of urea, 30 mol% of nitric acid, 2ml of solvent tetrahydrofuran and 0.4mmol of phenol into a reaction tube of an O catalyst, reacting at 70 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 70%.
Synthesis example 16
Synthesis of benzyl hexanoate
At a concentration of 40 mol% Fe2O3Adding 0.2mmol of n-caproamide, 40 mol% of duck warmer, 2ml of solvent toluene and 0.2mmol of phenol into a reaction tube of a catalyst, reacting at 70 ℃, washing with water or saturated salt solution after the reaction is finished, extracting with chloroform, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating the crude product by column chromatography to obtain a target product: the yield was 81%.
Claims (3)
1. A synthesis method of an ester (I) compound with the following structural formula comprises the following operation steps: adding different knots into a reaction vessel filled with iron saltAdding a catalytic amount of acid and a solvent into the amide and the alcohol, stirring at a proper reaction temperature, washing with water or a saturated salt solution after the reaction is finished, extracting with an organic solvent, drying, distilling under reduced pressure and concentrating to remove the solvent, and separating a crude product by column chromatography to obtain a target product (A)I）：
The reaction temperature is mainly 25-120 ℃,
the acid is one or more than two selected from benzoic acid, phenylacetic acid, benzenesulfonic acid, trifluoroacetic acid, naphthylacetic acid, concentrated hydrochloric acid and concentrated nitric acid;
the organic solvent is selected fromN,NDimethylformamide, n-hexane, cyclohexane, dimethyl sulfoxide, acetonitrile, 1, 4-dioxane, tetrahydrofuran, toluene,N-one or more of methyl pyrrolidone, chlorobenzene, 1, 2-xylene or 1, 2-dichloroethane;
the iron salt is selected from Fe and Fe2O3、Fe3O4、FeCl2、FeCl3、FeCl3·6H2O、Fe(NO3)3·6H2O、Fe2(SO4)3·H2One or more than two of O;
in the structural formula (I):
r is phenyl, 4-methylphenyl, 4-nitrophenyl, 4-hydroxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 4-trifluoromethylphenyl, 4-cyanophenyl, 3-methylphenyl, 2-thienyl, 2-pyridyl, 1-naphthyl;
R1is ethyl, isoamyl, tert-butyl, cyclopentyl, cyclohexyl, benzyl, p-methylbenzyl, 4-bromophenyl, naphthylmethyl;
the amide substrate is any one of benzamide, 4-methylbenzamide, 4-nitrobenzamide, 4-hydroxybenzamide, 4-fluorobenzamide, 4-chlorobenzamide, 4-bromobenzamide, 4-iodobenzamide, 4-trifluoromethylbenzamide, 4-cyanobenzamide, 3-methylbenzamide, 2-thiophenebenzamide, 2-pyridinebenzamide and 1-naphthamide.
2. The method for synthesizing esters (I) with the following structural formula as claimed in claim 1, wherein the molar ratio of amide, Fe salt and acid is 1: [0.1-1.0]: [0.1-1.0 ].
3. The method for synthesizing esters (I) compounds of the following formula according to claim 1, wherein the alcohol is any one of ethanol, isopropanol, isoamyl alcohol, tert-butyl alcohol, cyclopentanol, cyclohexanol, benzyl alcohol, p-methylbenzyl alcohol, p-bromobenzyl alcohol, and naphthalenemethanol.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4055590A (en) * | 1975-06-26 | 1977-10-25 | Rohm Gmbh | Method of making carboxylic acid esters |
| CN101440035A (en) * | 2007-11-22 | 2009-05-27 | 中国科学院兰州化学物理研究所 | Method for synthesizing organic carbonic ether |
| CN103687841A (en) * | 2011-08-19 | 2014-03-26 | 赢创罗姆有限公司 | Method for producing alpha-hydroxycarboxylic acid esters |
| CN107417594A (en) * | 2017-05-08 | 2017-12-01 | 凯莱英医药集团（天津）股份有限公司 | A kind of method of acid amides alcoholysis |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4055590A (en) * | 1975-06-26 | 1977-10-25 | Rohm Gmbh | Method of making carboxylic acid esters |
| CN101440035A (en) * | 2007-11-22 | 2009-05-27 | 中国科学院兰州化学物理研究所 | Method for synthesizing organic carbonic ether |
| CN103687841A (en) * | 2011-08-19 | 2014-03-26 | 赢创罗姆有限公司 | Method for producing alpha-hydroxycarboxylic acid esters |
| CN107417594A (en) * | 2017-05-08 | 2017-12-01 | 凯莱英医药集团（天津）股份有限公司 | A kind of method of acid amides alcoholysis |
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