CN115093378A - Preparation method of 2-thiazolidinone - Google Patents
Preparation method of 2-thiazolidinone Download PDFInfo
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- CN115093378A CN115093378A CN202210856514.1A CN202210856514A CN115093378A CN 115093378 A CN115093378 A CN 115093378A CN 202210856514 A CN202210856514 A CN 202210856514A CN 115093378 A CN115093378 A CN 115093378A
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- CN
- China
- Prior art keywords
- chloroform
- thiazolidinone
- reaction
- triphosgene
- cysteamine hydrochloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- SLYRGJDSFOCAAI-UHFFFAOYSA-N 1,3-thiazolidin-2-one Chemical compound O=C1NCCS1 SLYRGJDSFOCAAI-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 48
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 18
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229940097265 cysteamine hydrochloride Drugs 0.000 claims abstract description 13
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 11
- 150000004714 phosphonium salts Chemical group 0.000 claims abstract description 10
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 10
- DSUKUFGNCZKNGB-UHFFFAOYSA-N 2H-1,3-thiazol-2-ide 1-oxide Chemical compound S1([C-]=NC=C1)=O DSUKUFGNCZKNGB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 5
- 239000011230 binding agent Substances 0.000 claims abstract description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 48
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 claims description 3
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 claims description 2
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 abstract description 7
- 239000006227 byproduct Substances 0.000 abstract description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract description 2
- 239000002351 wastewater Substances 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 description 14
- 238000001816 cooling Methods 0.000 description 9
- 239000010413 mother solution Substances 0.000 description 7
- 239000012452 mother liquor Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000012265 solid product Substances 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- OCVLSHAVSIYKLI-UHFFFAOYSA-N 3h-1,3-thiazole-2-thione Chemical compound SC1=NC=CS1 OCVLSHAVSIYKLI-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229960003151 mercaptamine Drugs 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 239000005959 Fosthiazate Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- DUFVKSUJRWYZQP-UHFFFAOYSA-N fosthiazate Chemical compound CCC(C)SP(=O)(OCC)N1CCSC1=O DUFVKSUJRWYZQP-UHFFFAOYSA-N 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- -1 thiazole compound Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/34—Oxygen atoms
Abstract
The invention relates to a preparation method of 2-thiazolidone, which comprises the steps of uniformly mixing cysteamine hydrochloride, acid-binding agent sodium carbonate, quaternary ammonium salt or quaternary phosphonium salt catalyst and chloroform, adding mixed liquid of triphosgene and chloroform, heating to 25-45 ℃, reacting for 4-13 h, and carrying out post-treatment on reaction liquid after the reaction is finished. The method has less side reaction, and improves purity and yield; the carbonate is used as an acid-binding agent, no wastewater is generated in the production process, the pollution is reduced, the organic solvent used in the reaction and recrystallization processes can be recycled, the byproduct salt can be directly sold, and the cost is saved. The yield of the 2-thiazolidinone synthesized by the method is more than 91 percent, and the purity is more than 99 percent.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a preparation method of 2-thiazolidinone.
Background
The thiazole compounds have wide application in the fields of pesticide, medicine and the like, and the derivatives thereof have broad-spectrum biological activity and antiviral propertyIt has antibacterial, pesticidal, and herbicidal effects. 2-thiazolidinone (formula: C) 3 H 5 NOS, molecular weight: 103.14) is an important thiazole compound which can be directly used as a bactericide, an insecticide and a plant growth regulator, and is an important intermediate of pesticide, medicine and dye, and is an important intermediate of excellent nematicide fosthiazate. Therefore, the synthesis and research of the 2-thiazolidinone have important practical significance.
The prior literature reports that the synthesis methods of 2-thiazolidinone are more, and the two common methods are mainly two, namely a synthesis route taking 2-thiazolethione as a raw material: the method for preparing the 2-thiazolidinone by reacting the 2-thiazolethione with hydrogen peroxide, phosgene or ethylene oxide has the advantages of low yield, difficult control of the reaction process, extreme toxicity of the phosgene, low safety, easy polymerization and difficult treatment of a byproduct, namely ethylene sulfide generated by using the ethylene oxide, and difficult realization of clean production. The other method is to prepare 2-thiazolidinone by taking cysteamine as a raw material: and (3) carrying out cyclization reaction on cysteamine or cysteamine hydrochloride and one-carbon reagents such as thiourea, carbon monoxide, phosgene, imidazolone and the like. However, the method generally has the problems of low yield, high safety factor requirement, high cost, difficult actual operation and the like, and is not beneficial to industrial production.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a preparation method of 2-thiazolidinone, which has the advantages of low cost, high yield, cleanness, environmental protection and safe and simple operation.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of 2-thiazolidinone comprises the steps of uniformly mixing raw materials of cysteamine hydrochloride, acid-binding agent sodium carbonate, quaternary ammonium salt or quaternary phosphonium salt catalysts and solvent chloroform, adding mixed liquid of triphosgene and solvent chloroform, heating to 25-45 ℃, reacting for 4-13 hours, and carrying out aftertreatment on reaction liquid after the reaction is finished.
Specifically, the quaternary ammonium salt or quaternary phosphonium salt catalyst is one or more than two of tetrabutylammonium bromide, tetrabutylammonium chloride, benzyltriethylammonium bromide, benzyltriethylammonium chloride, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride and the like.
Further, the molar ratio of the cysteamine hydrochloride to the quaternary ammonium salt or quaternary phosphonium salt catalyst is 1: 0.008 to 0.05, preferably 1: 0.009-0.02.
Specifically, the molar ratio of the cysteamine hydrochloride to the triphosgene and the sodium carbonate is 1: 0.3-0.8: 3-6, preferably 1: 0.3-0.5: 3 to 5.
Further, the dosage of the chloroform is 1-5 times of the sum of the mass of the cysteamine hydrochloride, the sodium carbonate, the quaternary ammonium salt or quaternary phosphonium salt catalyst and the triphosgene.
Further, the post-treatment specifically comprises: centrifuging the reaction solution to obtain mother solution, distilling to recover chloroform as solvent, adding ethyl acetate to dissolve after the materials are all crystallized, and recrystallizing to obtain pure 2-thiazolidinone. Chloroform can be used as solvent.
Further, the mixed solution of triphosgene and chloroform is added in a dropwise manner, and the temperature is controlled not to exceed 15 ℃ in the dropwise adding process.
The preparation method of the 2-thiazolidinone comprises the following steps: adding cysteamine hydrochloride, sodium carbonate, quaternary ammonium salt or quaternary phosphonium salt catalyst and chloroform into a flask, stirring uniformly, dropwise adding mixed liquid of triphosgene and chloroform, controlling the temperature to be not higher than 15 ℃ in the dropwise adding process, heating to 25 ℃ after dropwise adding is finished, preserving heat for 3-8 h, heating to 35-45 ℃ again, preserving heat for 1-5 h, and after the reaction is finished, centrifuging the reaction liquid to obtain sodium chloride, sodium bicarbonate, excessive sodium carbonate solid and mother liquor; putting the obtained mother liquor into a flask, stirring and heating, distilling at normal pressure to recover chloroform, cooling to below 50 ℃, and vacuumizing (the pressure is-0.09 MPa) until the materials are completely crystallized. The pure 2-thiazolidinone can be obtained after twice recrystallization.
The recrystallization operation is specifically as follows: adding ethyl acetate, stirring, heating to reflux, refluxing for 1h, cooling to 60-70 deg.C, vacuum filtering, placing the filtrate in a crystallization kettle, stirring, cooling to room temperature, centrifuging to obtain solid product and mother liquor containing ethyl acetate, and drying under negative pressure to obtain the final product. And performing secondary recrystallization on the obtained product to obtain a pure product, wherein the yield is over 91 percent, and the purity is over 99 percent. The mother liquor containing ethyl acetate can be distilled under normal pressure to recover ethyl acetate for recycling.
The reaction equation of the synthetic method of the invention is as follows:
compared with the prior art, the synthesis method has the following beneficial effects:
the method adopts the solid phosgene, is safe and convenient to use, and has easy reaction operation; the side reaction is less, and the purity and the yield are improved; the carbonate is used as an acid-binding agent, no wastewater is generated in the production process, the pollution is reduced, the organic solvent used in the reaction and recrystallization processes can be recycled, the byproduct salt can be directly sold, and the cost is saved. The yield of the 2-thiazolidinone synthesized by the method is more than 91 percent, and the purity is more than 99 percent.
Detailed Description
The technical solution of the present invention is further described in detail with reference to the following examples, but the scope of the present invention is not limited thereto.
In the examples of the present invention, all the raw materials are general commercial products which can be purchased directly, unless otherwise specified.
Example 1
A preparation method of 2-thiazolidone specifically comprises the following steps:
(1) adding 9g (0.030 mol) of triphosgene into 20mL of chloroform, stirring until the triphosgene is completely dissolved, and pouring the solution into a constant-pressure funnel for later use;
(2) putting 10g (0.088 mol) of cysteamine hydrochloride, 30g (0.283 mol) of sodium carbonate and 0.22g (0.965 mmol) of benzyltriethylammonium chloride (TEBA) into a 250mL three-neck flask, adding 50mL of chloroform, uniformly stirring, dropwise adding the mixed solution of the triphosgene and the chloroform in the step (1), controlling the temperature to be not higher than 15 ℃ in the dropwise adding process, raising the temperature to 25 ℃ after the dropwise adding is finished, preserving the heat for 4h, raising the temperature to 45 ℃ again, preserving the heat for 1h, and finishing the reaction;
(3) centrifuging the reaction solution to obtain mother solution, putting the obtained mother solution into a 250mL four-neck flask, stirring and heating, distilling at normal pressure to recover chloroform, cooling to below 50 ℃, and vacuumizing (the pressure is-0.09 MPa) until the materials are all crystallized. Adding 10g of ethyl acetate, stirring, heating to reflux, refluxing for 1h, then cooling to 60-70 ℃, carrying out suction filtration, placing the filtrate in a crystallization kettle, stirring, cooling to room temperature, centrifuging to obtain a solid crude product and a mother solution containing ethyl acetate, and drying under negative pressure (the pressure is-0.07 MPa, and the drying is carried out at 30 ℃ for 5 hours) to obtain 9.2g of a solid product;
(4) and (4) carrying out secondary recrystallization on the solid product obtained in the step (3) by using ethyl acetate to obtain 8.37g of a pure 2-thiazolidinone product, wherein the yield is 92.2% and the content is 99%. The mother liquor containing ethyl acetate can be concentrated and distilled under normal pressure (85 ℃), and the ethyl acetate is recovered and recycled.
Example 2
A preparation method of 2-thiazolidone specifically comprises the following steps:
(1) adding 10g (0.033 mol) of triphosgene into 20mL of chloroform, stirring until the triphosgene is completely dissolved, and pouring the solution into a constant-pressure funnel for later use;
(2) putting 10g (0.088 mol) of cysteamine hydrochloride, 35g (0.330 mol) of sodium carbonate and 0.28g (0.868 mmol) of tetrabutylammonium bromide TBAB into a 250mL three-neck flask, then adding 70mL of chloroform, stirring uniformly, dropwise adding the mixed solution of the triphosgene and the chloroform in the step (1), controlling the temperature to be not higher than 15 ℃ in the dropwise adding process, after the dropwise adding is finished, heating to 25 ℃ and preserving heat for 6h, then heating to 40 ℃ and preserving heat for 2h, and finishing the reaction;
(3) centrifuging the reaction solution to obtain mother solution, putting the obtained mother solution into a 250mL four-neck flask, stirring and heating, distilling at normal pressure to recover chloroform, cooling to below 50 ℃, and vacuumizing (the pressure is more than-0.09 MPa) until the materials are completely crystallized. Adding 10g of ethyl acetate, stirring, heating to reflux, refluxing for 1h, then cooling to 60-70 ℃, carrying out suction filtration, placing the filtrate in a crystallization kettle, stirring, cooling to room temperature, centrifuging to obtain a solid crude product and a mother solution containing ethyl acetate, and drying under negative pressure (the pressure is-0.07 MPa, and the temperature is 35 ℃ for 4 hours) to obtain 9.1g of a solid product;
(4) and (4) carrying out secondary recrystallization on the solid product obtained in the step (3) by using ethyl acetate to obtain 8.3g of 2-thiazolidone pure product, wherein the yield is 91.4%, and the content is 99%. The mother liquor containing ethyl acetate can be concentrated and distilled under normal pressure (85 ℃), and the ethyl acetate is recovered and recycled.
Example 3
Referring to example 1, the difference from example 1 is that: in the step (2), tetrabutyl phosphonium bromide is selected as a catalyst. The yield of the pure product of the prepared 2-thiazolidinone is 93.2 percent, and the content is 99 percent.
Claims (7)
1. A preparation method of 2-thiazolidone is characterized by mixing cysteamine hydrochloride, acid-binding agent sodium carbonate, quaternary ammonium salt or quaternary phosphonium salt catalyst and chloroform uniformly, adding mixed liquid of triphosgene and chloroform, heating to 25-45 ℃ for reaction for 4-13 h, and carrying out post-treatment on reaction liquid after the reaction is finished to obtain the 2-thiazolidone.
2. The process for producing 2-thiazolidinone according to claim 1 wherein the quaternary ammonium salt or quaternary phosphonium salt catalyst is one or more of tetrabutylammonium bromide, tetrabutylammonium chloride, benzyltriethylammonium bromide, benzyltriethylammonium chloride, tetrabutylphosphonium bromide and tetrabutylphosphonium chloride.
3. A process for preparing 2-thiazolidinone according to claim 2 wherein the molar ratio of cysteamine hydrochloride to quaternary ammonium salt or quaternary phosphonium salt catalyst is 1: 0.008 to 0.05.
4. The method of preparing 2-thiazolidinone according to claim 1 wherein the molar ratio of cysteamine hydrochloride to triphosgene and sodium carbonate is 1: 0.3-0.8: 3 to 6.
5. The method of preparing 2-thiazolidinone according to claim 1, wherein the amount of chloroform is 1 to 5 times of the sum of the mass of cysteamine hydrochloride, sodium carbonate, quaternary ammonium salt or quaternary phosphonium salt catalyst and triphosgene.
6. A process for the preparation of 2-thiazolidinone according to claim 1 wherein the post-treatment is specifically: centrifuging the reaction liquid to obtain mother liquid, distilling to recover chloroform as solvent, adding ethyl acetate to dissolve after the materials are all crystallized, and recrystallizing to obtain pure 2-thiazolidinone.
7. A process for preparing 2-thiazolidinone according to claim 1 wherein the mixture of triphosgene and chloroform is added dropwise at a temperature not exceeding 15 ℃.
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85106755A (en) * | 1984-06-30 | 1987-01-21 | 田道制药株式会社 | Tetrahydrothiazole derivates and preparation method |
| CN1033625A (en) * | 1987-12-14 | 1989-07-05 | 里查德奇特昂凡昔的古阿脱 | 2-thiazolidone analog derivative, the pharmaceutical compositions that contains this derivative and manufacture method thereof |
| JPH09176137A (en) * | 1995-03-02 | 1997-07-08 | Sankyo Co Ltd | Optically active thiazolidinone derivative |
| CN101801943A (en) * | 2007-09-14 | 2010-08-11 | 拜尔农作物科学股份公司 | Process for preparing cyanimino-1,3-thiazolidines |
| CN101880262A (en) * | 2010-06-23 | 2010-11-10 | 山东理工大学 | Preparation method of 2-thiazolidine ketone |
| CN102702263A (en) * | 2012-05-24 | 2012-10-03 | 山东华阳农药化工集团有限公司 | New process for synthetizing lythidathion |
| CN103450109A (en) * | 2012-06-05 | 2013-12-18 | 成都市考恩斯科技有限责任公司 | Preparation method of nitrogen-sulfur heterocyclic ketone |
| CN104592146A (en) * | 2015-01-19 | 2015-05-06 | 烟台腾辉化工有限公司 | Preparation process of L-2-oxothiazolidine-4-carboxylic acid |
| CN110563666A (en) * | 2019-09-26 | 2019-12-13 | 安徽工业大学 | Preparation method of 2-thiazolidinone |
-
2022
- 2022-07-21 CN CN202210856514.1A patent/CN115093378B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85106755A (en) * | 1984-06-30 | 1987-01-21 | 田道制药株式会社 | Tetrahydrothiazole derivates and preparation method |
| CN1033625A (en) * | 1987-12-14 | 1989-07-05 | 里查德奇特昂凡昔的古阿脱 | 2-thiazolidone analog derivative, the pharmaceutical compositions that contains this derivative and manufacture method thereof |
| JPH09176137A (en) * | 1995-03-02 | 1997-07-08 | Sankyo Co Ltd | Optically active thiazolidinone derivative |
| CN101801943A (en) * | 2007-09-14 | 2010-08-11 | 拜尔农作物科学股份公司 | Process for preparing cyanimino-1,3-thiazolidines |
| CN101880262A (en) * | 2010-06-23 | 2010-11-10 | 山东理工大学 | Preparation method of 2-thiazolidine ketone |
| CN102702263A (en) * | 2012-05-24 | 2012-10-03 | 山东华阳农药化工集团有限公司 | New process for synthetizing lythidathion |
| CN103450109A (en) * | 2012-06-05 | 2013-12-18 | 成都市考恩斯科技有限责任公司 | Preparation method of nitrogen-sulfur heterocyclic ketone |
| CN104592146A (en) * | 2015-01-19 | 2015-05-06 | 烟台腾辉化工有限公司 | Preparation process of L-2-oxothiazolidine-4-carboxylic acid |
| CN110563666A (en) * | 2019-09-26 | 2019-12-13 | 安徽工业大学 | Preparation method of 2-thiazolidinone |
Non-Patent Citations (4)
| Title |
|---|
| HAI-XIA SONG等: "Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3", 《CHEM. EUR. J.》, vol. 25, pages 10907 - 10912 * |
| M. D\'ISCHIA等: "A Facile Syntesis of 2-Oxo-Thiazolidines of Biological Interest", 《SYNTHETIC COMMUNICATIONS》, vol. 17, no. 13, pages 1577 - 1585 * |
| 刘秀明: "2-噻唑硫（烷）酮衍生物的合成", 《中国优秀硕士学位论文全文数据库 工程科技I辑》, no. 3, pages 016 - 15 * |
| 王高磊等: "含硫醚结构新烟碱类化合物的合成及杀虫活性", 《济南大学学报（自然科学版）》, vol. 25, no. 2, pages 175 - 178 * |
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