CN109912475A - A kind of environment-friendly preparation method thereof of Z-3- thiocyanate groups acrylamide compound - Google Patents
A kind of environment-friendly preparation method thereof of Z-3- thiocyanate groups acrylamide compound Download PDFInfo
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- CN109912475A CN109912475A CN201910228054.6A CN201910228054A CN109912475A CN 109912475 A CN109912475 A CN 109912475A CN 201910228054 A CN201910228054 A CN 201910228054A CN 109912475 A CN109912475 A CN 109912475A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 62
- -1 propine amide compound Chemical class 0.000 claims abstract description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 31
- 239000004310 lactic acid Substances 0.000 claims abstract description 31
- 238000007259 addition reaction Methods 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 10
- 238000010790 dilution Methods 0.000 claims abstract description 3
- 239000012895 dilution Substances 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical group [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims description 19
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 15
- 229940116357 potassium thiocyanate Drugs 0.000 claims description 14
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- HCJTYESURSHXNB-UHFFFAOYSA-N propynamide Chemical class NC(=O)C#C HCJTYESURSHXNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- MJTDYWXUZKOVHX-UHFFFAOYSA-N n-phenylprop-2-ynamide Chemical compound C#CC(=O)NC1=CC=CC=C1 MJTDYWXUZKOVHX-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- 239000011831 acidic ionic liquid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ZLQULXQLBYUISA-UPHRSURJSA-N [(z)-3-amino-3-oxoprop-1-enyl] thiocyanate Chemical class NC(=O)\C=C/SC#N ZLQULXQLBYUISA-UPHRSURJSA-N 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001361 allenes Chemical class 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZTHRQJQJODGZHV-UHFFFAOYSA-N n-phenylpropanamide Chemical compound CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 125000002009 alkene group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- 238000010490 three component reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of environment-friendly preparation method thereofs of Z-3- thiocyanate groups acrylamide compound.Under ultrasonic wave effect, lactic acid is catalyzed propine amide compound, rhodanate and water and carries out three component addition reactions, generates Z-3- thiocyanate groups acrylamide compound;After reaction, water dilution is added into system, high-purity Z-3- thiocyanate groups acrylamide product can be precipitated;This method good product selectivity, high income, separation process is simple, catalyst low cost, environmentally friendly, is conducive to industrialized production and application.
Description
Technical Field
The invention relates to a green preparation method of a Z-3-thiocyanoacrylamide compound, in particular to a method for synthesizing the Z-3-thiocyanoacrylamide compound by catalyzing one-step addition reaction of a propiolic amide compound, thiocyanate and water by using ultrasonic-assisted lactic acid, and belongs to the technical field of synthesis of organic intermediates.
Background
The Z-3-thiocyanato acrylamide compound not only has very important physiological activity, but also contains thiocyanate functional groups, alkenyl groups and amide groups which are all important modifiable functional groups, and is a very important medicine and organic synthesis intermediate compound. In the prior art, acidic ionic liquid is used for catalyzing three-component reaction of propynamide, thiocyanate and water to obtain Z-3-thiocyanoacrylamide compound (Green chem. 2018,20,3683), but the reaction has the following defects, and the practical application of the reaction is limited:
1) the acidic ionic liquid is toxic, the preparation process is not environment-friendly, the cost is high, and no commercial product is available.
2) The yield of the Z-3-thiocyanoacrylamide compound is 81-83%, and the E-isomer, the propiolic acid which is the decomposition product of the propiolamide and the unreacted propiolamide raw material exist in the reaction, so that the purity is not high.
3) The separation of the product needs to use volatile organic solvent for extraction, the purification of the product needs to be separated by silica gel column chromatography, the separation process is not only complex and high in cost, but also can cause environmental pollution.
4) The acidic ionic liquid circulates for 5 times, the efficiency is reduced by 13 percent, and the use cost is higher.
The specific conditions of the existing method for synthesizing the Z-3-thiocyanato acrylamide compound by catalyzing three components of propynamide, thiocyanate and water to react by using the acidic ionic liquid are as follows:
disclosure of Invention
Aiming at the technical problems existing in the synthesis and separation of Z-3-thiocyanoacrylamide compounds in the prior art, the invention aims to provide a method for synthesizing the Z-3-thiocyanoacrylamide compound by catalyzing the one-pot reaction of propiolamide compound, thiocyanate and water by using non-toxic and cheap lactic acid.
In order to achieve the technical purpose, the invention provides a green preparation method of a Z-3-thiocyanatoacrylamide compound, which is characterized in that under the action of ultrasonic waves, lactic acid is used for catalyzing a propiolic amide compound, thiocyanate and water to carry out addition reaction to obtain the Z-3-thiocyanatoacrylamide compound.
Preferably, the propiolamide compound has the structure of formula 1;
the Z-3-thiocyanatoacrylamide compound has the structure of formula 2:
wherein,
r is selected from alkyl or aryl
In a preferred embodiment, R may be alkyl, such as C1~C10Alkyl, e.g. straight-chain alkyl, may also be branched, or C3~C7And cycloalkyl groups such as methyl, ethyl, isobutyl, cyclohexyl and the like. R can be aryl, specifically, the aryl is phenyl or substituted phenyl containing common substituent groups on benzene ring, and the substituted phenyl is phenyl containing common substituent groups on benzene ring, such as C1~C5Short-chain alkyl of, C1~C5Alkoxy, halogen substituent (fluorine, chlorine, bromine, etc.), trifluoromethyl, nitro, cyano, amino, C2~C5Ester group and hydroxyl group. The position of the substituent is not limited, and the number of the substituents may be 1 or more, and generally one substituent is contained.
In a preferred embodiment, the thiocyanate may be a soluble salt such as potassium thiocyanate, sodium thiocyanate, or the like. Most preferably potassium thiocyanate.
Preferably, the molar ratio of the propiolamide compound to the potassium thiocyanate to the water to the lactic acid is 1:1 to 2:2 to 5. The most preferred molar ratio is 1:1.2:1: 4.
In a preferred embodiment, the addition reaction conditions are as follows: at room temperature, the ultrasonic power is 25-45W, the ultrasonic frequency is 28 KHz-60 KHz, and the reaction time is 15-40 min. A further preferred ultrasonic power is 35W. A further preferred ultrasound frequency is 40 KHz. The addition reaction of the propiolamide compound, thiocyanate and water is catalyzed by lactic acid under the assistance of the preferable ultrasonic condition, so that the reaction time is shortened, and the conversion rate can be improved.
Preferably, after the addition reaction is finished, water is added into the reaction system for dilution, a Z-3-thiocyanatoacrylamide product is separated out, and the product is separated from the lactic acid aqueous solution through liquid separation or filtration, so that the Z-3-thiocyanatoacrylamide compound product is obtained. The invention adopts water to dilute the reaction mixed product, so that the high-purity Z-3-thiocyanatoacrylamide compound can be separated out, the traditional organic solvent extraction and silica gel column chromatography separation method are not needed, and the use of volatile organic solvent is completely avoided.
Preferably, the amount of water added is more than 5 times the mass of the lactic acid. Preferably 5 times or more by mass of water, to ensure smooth precipitation of the Z-3-thiocyanatoacrylamide compound.
The lactic acid adopted by the invention is used as a catalyst and a reaction medium in the addition reaction.
The route of synthesizing the Z-3-thiocyanato acrylamide compound by the addition reaction of propiolamide compound, thiocyanate (taking potassium thiocyanate as an example) and water is as follows:
the specific reaction principle is shown in the following reaction formula, lactic acid firstly activates propynamide compound to obtain a allene intermediate IM2, thiocyanate radical nucleophilically attacks β -carbon atom of the allene intermediate IM2 and then forms intermolecular hydrogen bond with lactic acid to obtain an intermediate IM3, and the intermediate IM3 captures proton generated by ionization of water molecule from the reverse direction of the hydrogen bond to obtain a trans-addition product Z-3-thiocyanato acrylamide compound.
Compared with the prior art, the technical scheme of the invention has the beneficial technical effects that:
1) the invention adopts lactic acid as a reaction medium and a catalyst, is easy to recycle, safe, nontoxic, environment-friendly, easily available in source and low in price.
2) The invention reacts under room temperature with mild condition.
3) The propiolic amide compound has wide selectivity and good functional group compatibility, and is easy for modification of various groups.
4) The invention uses ultrasonic wave to promote the reaction, shortens the reaction time, quantifies the conversion rate of raw materials, has 100 percent of product selectivity, and does not generate E-type isomer in the reaction.
5) According to the invention, only 5 times of water by mass of lactic acid needs to be added into the reaction mixture, the product can be separated out in a layered manner, and the pure product is obtained, so that the problem that the separation and purification process of the synthesized Z-3-thiocyanato acrylamide compound in the prior art is complex is solved.
6) The lactic acid can be recycled for 5 times, the efficiency is reduced by 3 percent, and the high catalytic activity is kept, so that the method has obvious advantages compared with the acidic ionic liquid.
7) The Z-3-thiocyanato acrylamide compound has thiocyanato acid functional groups with important physiological activity, modifiable alkene groups, amide groups and the like, and provides important organic intermediates for the synthesis of medicaments and organic matters.
Detailed Description
The following specific examples are intended to further illustrate the present disclosure, but not to limit the scope of the claims.
Comparative example:
the following control experiment groups 1 to 19 all react according to the following reaction equation:
the specific operation steps are as follows: in a 20mL reaction tube, N-phenyl propiolamide (1 equivalent, 10mmol), thiocyanate, water and biological acid were added in sequence, and the obtained mixed solution was reacted in an ultrasonic reaction apparatus for 30 min. After the reaction is finished, 18ml of water is added to obtain the target product.
In the table, the influence of various thiocyanic acid sources on the addition reaction of the N-phenyl propynamide, the potassium thiocyanate and the water is investigated by experimental groups 1-3, and the experimental data show that the efficiency of the addition reaction of the three components can be obviously improved by cheap potassium thiocyanate relative to sodium thiocyanate or ammonium thiocyanate and the like.
In the table, experiment groups 1 and 4-5 investigate the influence of the dosage of the reaction raw material KSCN on the addition reaction of three components of N-phenyl propynamide, potassium thiocyanate and water, and experiments show that the optimal molar dosage of the KSCN is 1.2 equivalent; when the amount of KSCN is too low, the yield of the target product is reduced, and when the KSCN is further increased, the yield of the target product is not increased.
In the table, experiment groups 1 and 6-7 investigate the influence of the amount of reaction raw material water on the addition reaction of three components, namely N-phenyl propynamide, potassium thiocyanate and water, and experiments show that the optimal molar amount of KSCN is 1 equivalent; when the amount of water is too low, the yield of the target product decreases, and when the amount of water is further increased, the yield of the target product does not increase.
In the table, experimental groups 8-13 investigate the influence of various reaction media on the addition reaction of three components, namely N-phenyl propynamide, potassium thiocyanate and water, and experimental data show that the reaction in a lactic acid medium can obviously improve the efficiency of the addition reaction of the three components compared with other reaction media, and the reaction has single reaction addition selectivity.
In the table, experiment groups 1 and 14-15 investigate the influence of the dosage of the lactic acid on the addition reaction of three components, namely N-phenyl propynamide, potassium thiocyanate and water, and experiments show that the optimal molar dosage of the lactic acid is 4 equivalents; when the amount of lactic acid is more than 4 equivalents, the reaction efficiency is not improved; when the amount of lactic acid used is less than 4 equivalents, the yield of the objective product decreases.
In the table, experiment groups 1 and 16-19 investigate the influence of ultrasonic assistance on the co-addition reaction of N-phenyl propynamide, potassium thiocyanate and water, and experiments show that the reaction time can be greatly shortened and the reaction efficiency can be improved through the ultrasonic assistance reaction, particularly when the ultrasonic power is 35W/frequency is 40KHz, the co-addition reaction effect is optimal, and the optimal target product yield can be obtained in a short time.
Results of the cycle experiment
N-phenylpropionamide (10mmol), potassium thiocyanate (12mmol, 1.16g), water (10mmol, 0.18g), and lactic acid (40mmol, 3.60g) were sequentially added to a 20mL reaction tube, and the resulting mixture was reacted for 30 minutes in a 35W/40KHz ultrasonic reaction apparatus. After the reaction, 18ml of water was added to form an aqueous lactic acid solution together with lactic acid, and Z-3-thiocyanatoacrylamide was insoluble in the aqueous lactic acid solution, precipitated, separated, and dried in vacuo to calculate the weight. The water in the aqueous lactic acid solution was removed under reduced pressure and used directly in the next cycle, and the yield data obtained were as follows.
1 | 2 | 3 | 4 | 5 |
94% | 94% | 93% | 92% | 91% |
Examples 1 to 2
The following examples 1-2 were all reacted according to the following reaction equation:
the specific operation steps are as follows: to a 20mL reaction tube, propynamide (10mmol), potassium thiocyanate (12mmol, 1.16g), water (10mmol, 0.18g), and lactic acid (40mmol, 3.60g) were added in this order, and the resulting mixture was reacted for 30 minutes in a 35W/40KHz ultrasonic reaction apparatus. After the reaction, 18ml of water was added to form an aqueous lactic acid solution together with lactic acid, and Z-3-thiocyanatoacrylamide was insoluble in the aqueous lactic acid solution, precipitated, separated, and dried in vacuo to calculate the weight.
Example 1
Raw materials:and (3) target products:
Z-N-octyl-3-thiocyanatoacrylamide:
the yield was 93%.
1H NMR(400MHz,CDCl3)δ7.16(d,J=10.0Hz,1H),6.33(d,J=10.0Hz,1H), 5.82(brs,1H),3.34(q,J=6.8Hz,2H),1.57–1.50(m,2H),1.33–1.27(m,2H),2.54 (t,J=6.8Hz,3H).
13C NMR(100MHz,CDCl3)δ162.1,126.3,125.9,107.5,39.9,31.8,29.5,29.2,29.0, 26.9,22.7,14.2.
Example 2
Raw materials:and (3) target products:
Z-N-phenyl-3-thiocyanatoacrylamide:
the yield was 94%.
1H NMR(400MHz,CDCl3)δ8.17(d,J=6.4Hz,1H),7.58–7.55(m,2H),7.46–7.42 (m,2H),7.35–7.30(m,1H),6.33(d,J=6.4Hz,1H).
13C NMR(100MHz,CDCl3)δ167.7,139.6,136.5,129.4,128.8,127.6,124.8,114.8。
Claims (8)
1. A green preparation method of Z-3-thiocyanato acrylamide compound is characterized by comprising the following steps: under the action of ultrasonic waves, lactic acid catalyzes propynamide compounds, thiocyanate and water to carry out addition reaction to obtain Z-3-thiocyanato acrylamide compounds.
2. The green process for producing a Z-3-thiocyanatoacrylamide compound according to claim 1, characterized in that:
the propiolamide compound has a structure of formula 1;
the Z-3-thiocyanatoacrylamide compound has the structure of formula 2:
wherein,
r is alkyl or aryl.
3. The green process for producing a Z-3-thiocyanatoacrylamide compound according to claim 2, characterized in that:
the alkyl group includes C1~C10An alkyl group;
the aryl group comprising phenyl, or containing C1~C5Alkyl, halogen, nitro, cyano, amino, C2~C5Ester group, hydroxyl group, trifluoromethyl group, C1~C5Phenyl group as at least one substituent of the alkoxy group of (1).
4. The green process for producing a Z-3-thiocyanatoacrylamide compound according to claim 1, characterized in that: the thiocyanate is potassium thiocyanate and/or sodium thiocyanate.
5. The green process for producing a Z-3-thiocyanatoacrylamide compound according to claim 1, characterized in that: the molar ratio of the propiolamide compound to the thiocyanate to the water to the lactic acid is 1: 1-2: 2-5.
6. The green production method of a Z-3-thiocyanatoacrylamide compound according to any one of claims 1 to 5, characterized in that: the conditions of the addition reaction are as follows: at room temperature, the ultrasonic power is 25-45W, the ultrasonic frequency is 28 KHz-60 KHz, and the reaction time is 15-40 min.
7. The green production method of a Z-3-thiocyanatoacrylamide compound according to any one of claims 1 to 5, characterized in that: and after the addition reaction is finished, adding water into the reaction system for dilution, precipitating the Z-3-thiocyanatoacrylamide compound, and filtering or separating liquid to obtain the Z-3-thiocyanatoacrylamide compound.
8. The green process for producing a Z-3-thiocyanatoacrylamide compound according to claim 7, which comprises: the adding amount of water is more than 5 times of the mass of the lactic acid.
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CN109020855A (en) * | 2018-07-20 | 2018-12-18 | 湖南科技学院 | A kind of method of the halogenated -1- thiocyanate groups vinyl compound of ultrasonic-assisted synthesis Z-2- |
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CN109020855A (en) * | 2018-07-20 | 2018-12-18 | 湖南科技学院 | A kind of method of the halogenated -1- thiocyanate groups vinyl compound of ultrasonic-assisted synthesis Z-2- |
Non-Patent Citations (2)
Title |
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CHAO WU等: "Natural Deep Eutectic Solvent-Catalyzed Selenocyanation of Activated Alkynes via an Intermolecular H‑Bonding Activation Process", 《ACS SUSTAINABLE CHEM.ENG.》 * |
CHAO WU等: "Ultrasound-promoted Brønsted acid ionic liquid-catalyzed hydrothiocyanation of activated alkynes under minimal solvent conditions", 《GREEN CHEMISTRY》 * |
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Application publication date: 20190621 |