CN114351174A - Preparation method of benzyl thiocyanate compound - Google Patents
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- CN114351174A CN114351174A CN202210111065.8A CN202210111065A CN114351174A CN 114351174 A CN114351174 A CN 114351174A CN 202210111065 A CN202210111065 A CN 202210111065A CN 114351174 A CN114351174 A CN 114351174A
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- ABNDFSOIUFLJAH-UHFFFAOYSA-N thiocyanatomethylbenzene Natural products N#CSCC1=CC=CC=C1 ABNDFSOIUFLJAH-UHFFFAOYSA-N 0.000 title claims abstract description 18
- -1 benzyl thiocyanate compound Chemical class 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- XLTUPERVRFLGLJ-UHFFFAOYSA-N isothiocyanato(trimethyl)silane Chemical class C[Si](C)(C)N=C=S XLTUPERVRFLGLJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002904 solvent Chemical class 0.000 claims abstract description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003792 electrolyte Chemical class 0.000 claims abstract description 3
- 150000005194 ethylbenzenes Chemical class 0.000 claims abstract description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000010898 silica gel chromatography Methods 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 2
- URFPRAHGGBYNPW-UHFFFAOYSA-N 1-bromo-4-ethylbenzene Chemical compound CCC1=CC=C(Br)C=C1 URFPRAHGGBYNPW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical class [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- 229940116357 potassium thiocyanate Drugs 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- XDKMXYYPKSWJNR-UHFFFAOYSA-N thiocyanic acid;triphenylphosphane Chemical compound SC#N.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 XDKMXYYPKSWJNR-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- QMGHHBHPDDAGGO-IIWOMYBWSA-N (2S,4R)-1-[(2S)-2-[[2-[3-[4-[3-[4-[[5-bromo-4-[3-[cyclobutanecarbonyl(methyl)amino]propylamino]pyrimidin-2-yl]amino]phenoxy]propoxy]butoxy]propoxy]acetyl]amino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide Chemical compound CN(CCCNC1=NC(NC2=CC=C(OCCCOCCCCOCCCOCC(=O)N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)NCC3=CC=C(C=C3)C3=C(C)N=CS3)C(C)(C)C)C=C2)=NC=C1Br)C(=O)C1CCC1 QMGHHBHPDDAGGO-IIWOMYBWSA-N 0.000 description 1
- PSWDQTMAUUQILQ-UHFFFAOYSA-N 2-[(6-methoxy-4-methylquinazolin-2-yl)amino]-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound N1=C(C)C2=CC(OC)=CC=C2N=C1NC1=NC(=O)C(C)=C(C)N1 PSWDQTMAUUQILQ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical class [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125796 compound 3d Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/09—Nitrogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/11—Halogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/29—Coupling reactions
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
Abstract
The invention discloses a preparation method of a benzyl thiocyanate compound, belonging to the technical field of organic synthesis. The method comprises the following steps: adding substituted ethylbenzene, trimethylsilyl isothiocyanate, electrolyte and solvent into a reactor, reacting under the action of constant current, and separating by silica gel column chromatography to obtain pure target product after the reaction is finished. The preparation method of the benzyl thiocyanate compound provided by the invention has the characteristics of scientificity, reasonableness, mild conditions, simplicity in operation and the like. The reaction equation is as follows:
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of a benzyl thiocyanate compound.
Background
Thiocyanide compounds are widely present in natural products and drug Molecules (eur.j.med.chem.,2016,118,21) and are also important intermediates for the synthesis of thiocarbamates, thiotetrazoles and other sulfur-containing derivatives (Molecules,2018,23, 2727). Researches show that the compounds have various biological activities such as sterilization, anticancer and the like, and have important application values in the fields of medicines, pesticides and the like. Therefore, the development of a new green and efficient method for synthesizing the thiocyanate compounds is of great significance.
The preparation method of the benzyl thiocyanate compound comprises the following steps:
1) halogenated alkane and potassium thiocyanate are used as raw materials
Varma et al prepared benzyl thiocyanate (J.org.chem.2006,71,6697) from haloalkane and potassium thiocyanate at microwave temperature of 110 deg.C.
2) Uses mercaptan and triphenylphosphine thiocyanate as raw materials
Iranpor et al prepared benzyl thiocyanate compounds from mercaptan and triphenylphosphine thiocyanate, the latter being generated in situ from triphenylphosphine, bromine and ammonium thiocyanate at room temperature (Tetrahedron Lett.2002,43,3439).
The benzyl thiocyanate compound synthesized by the method has obvious defects and shortcomings: 1) the starting material needs to be pre-functionalized; 2) the use of toxic reagents; 3) the reaction conditions were severe.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a preparation method of a benzylthiocyanate compound.
A method for preparing a benzyl thiocyanate compound, the benzyl thiocyanate compound having a structure represented by formula I:
in the formula I, wherein R1The substituent is fluorine, chlorine, bromine, methyl, ethyl, tertiary butyl, isopropyl, cyclohexyl, chloromethyl or cyano. Characterized in that the molar ratio of 1: 2, adding tetrabutylammonium perchlorate as electrolyte and dichloroethane as solvent into substituted ethylbenzene and trimethylsilyl isothiocyanate, and reacting at room temperature under the action of constant current, wherein the reaction equation is as shown in formula II:
the invention has the beneficial effects that: the invention establishes a new method for synthesizing the benzyl thiocyanate compounds, and the method has the characteristics of easily obtained raw materials, mild reaction conditions, wide substrate range and the like.
Drawings
FIG. 1 is an NMR spectrum of Compound 3a prepared in example 1;
FIG. 2 is an NMR spectrum of compound 3d prepared in example 7;
FIG. 3 is an NMR spectrum of compound 3i prepared in example 9.
Detailed Description
The invention is described in further detail below with reference to the following figures and specific examples:
the test methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1
Preparation of benzyl thiocyanate Compound 3a
To a 10mL three-necked flask were added p-bromoethylbenzene 1a (0.3mmol,56mg), trimethylsilyl isothiocyanate 2(0.6mmol,79mg), tetrabutylammonium perchlorate (0.6mmol,205mg) and dichloroethane (6 mL). Graphite felt (1cm x 1.5cm x 1cm) is used as an anode, and a platinum sheet (1cm x 1cm x 0.1mm) is used as a cathode. The reaction mixture was stirred at room temperature for 6 hours at a constant current of 5 mA. After completion of the reaction, the solvent was removed by rotary evaporator. Product 3a was obtained by column chromatography on silica gel using petroleum ether and dichloromethane (2:1) as eluent in 81% yield.
1H NMR(500MHz,CDCl3)δ7.52(d,J＝8.4Hz,2H),7.26(d,J＝8.4Hz,2H),4.55(q,J＝7.0Hz,1H),1.85(d,J＝7.0Hz,3H).
13C NMR(125MHz,CDCl3)δ138.3,132.3,128.8,123.1,111.4,47.8,21.8.
example 2
1a in example 1 is replaced by 1b, other conditions are the same as example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3b:
1H NMR(500MHz,CDCl3)δ7.30(d,J＝7.9Hz,2H),7.22(d,J＝7.9Hz,2H),4.61(q,J＝7.0Hz,1H),2.55–2.46(m,1H),1.88(d,J＝6.9Hz,3H),1.88–1.72(m,4H),1.47–1.36(m,4H),1.31–1.22(m,2H).
13C NMR(125MHz,CDCl3)δ149.1,136.3,127.6,127.1,112.1,48.6,44.3,34.4,26.9,26.2,22.2.
example 3
1a in example 1 is replaced by 1c, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3c:
1H NMR(500MHz,CDCl3)δ7.27(d,J＝8.3Hz,2H),7.19(d,J＝7.8Hz,2H),4.60(q,J＝6.9Hz,1H),2.35(s,3H),1.86(d,J＝7.0Hz,3H).
13C NMR(125MHz,CDCl3) Delta 139.0,136.1,129.8,127.1,112.0,48.6,22.1,21.3 example 4
1a in example 1 is replaced by 1d, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
1H NMR(500MHz,CDCl3)δ7.40(d,J＝8.4Hz,2H),7.31(d,J＝8.4Hz,2H),4.61(q,J＝7.0Hz,1H),1.88(d,J＝6.9Hz,3H),1.32(s,9H).
13C NMR(125MHz,CDCl3)δ152.2,136.0,126.9,126.1,112.1,48.5,34.8,31.3,22.2.
example 5
1a in example 1 is replaced by 1e, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3e:
1H NMR(500MHz,CDCl3)δ7.37(dd,J＝8.7,5.1Hz,2H),7.08(t,J＝8.5Hz,2H),4.60(q,J＝7.0Hz,1H),1.86(d,J＝7.0Hz,3H).
13C NMR(125MHz,CDCl3)δ162.9(d,J＝248.6Hz),135.1,129.0(d,J＝8.3Hz),116.2(d,J＝21.9Hz),111.6,47.8,22.1.
example 6
1f is used instead of 1a in example 1, the conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3f:
1H NMR(500MHz,CDCl3)δ7.37(d,J＝8.6Hz,2H),7.33(d,J＝8.6Hz,2H),4.57(q,J＝7.0Hz,1H),1.85(d,J＝7.0Hz,3H).
13C NMR(125MHz,CDCl3)δ137.8,135.0,129.4,128.5,111.4,47.8,21.9.
example 7
1a in example 1 was replaced by 1g, and the experimental results are shown in Table 1, except that the conditions were the same as in example 1.
3g of spectrogram analysis data:
1H NMR(500MHz,CDCl3)δ7.70(d,J＝8.4Hz,2H),7.51(d,J＝8.2Hz,2H),4.57(q,J＝7.1Hz,1H),1.87(d,J＝7.1Hz,3H).
13C NMR(125MHz,CDCl3) Delta 144.6,133.0,128.0,118.2,113.1,110.7,47.5,21.5 EXAMPLE 8
1a in example 1 is replaced by 1h, other conditions are the same as example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3h:
1H NMR(500MHz,CDCl3)δ7.42(d,J＝8.1Hz,2H),7.38(d,J＝8.3Hz,2H),4.62–4.59(m,1H),4.58(s,2H),1.87(d,J＝7.0Hz,3H).
13C NMR(125MHz,CDCl3) Delta 139.4,138.3,129.3,127.6,111.6,48.1,45.6,22.0 example 9
1a in example 1 is replaced by 1i, other conditions are the same as example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3i:
1H NMR(500MHz,CDCl3)δ7.30(d,J＝8.3Hz,2H),7.24(d,J＝8.3Hz,2H),4.61(q,J＝7.0Hz,1H),2.96–2.86(m,1H),1.88(d,J＝7.0Hz,3H),1.25(d,J＝6.9Hz,6H).
13C NMR(125MHz,CDCl3)δ150.0,136.4,127.3,127.2,112.1,48.6,34.0,23.9,22.2.
example 10
1j is used for replacing 1a in example 1, other conditions are the same as example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3j:
1H NMR(500MHz,CDCl3)δ7.30(d,J＝8.2Hz,2H),7.22(d,J＝7.9Hz,2H),4.61(q,J＝7.0Hz,1H),2.66(q,J＝7.6Hz,2H),1.88(d,J＝7.0Hz,3H),1.24(t,J＝7.6Hz,3H).
13C NMR(125MHz,CDCl3)δ145.4,136.3,128.7,127.2,112.1,48.7,28.7,22.2,15.5.
TABLE 1
Claims (2)
1. A method for preparing a benzyl thiocyanate compound, the benzyl thiocyanate compound having a structure represented by formula I:
in the formula I, wherein R1The substituent is fluorine, chlorine, bromine, methyl, ethyl, tertiary butyl, isopropyl, cyclohexyl, chloromethyl or cyano. Characterized in that the molar ratio of 1: 2, adding tetrabutylammonium perchlorate as electrolyte and dichloroethane as solvent into substituted ethylbenzene and trimethylsilyl isothiocyanate, and reacting at room temperature under the action of constant current, wherein the reaction equation is as shown in formula II:
2. the method of claim 1, wherein: the electrode is graphite felt as an anode and a platinum sheet as a cathode, the reaction time is 6h, and the current intensity is constant current of 5 mA.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111235596A (en) * | 2020-01-21 | 2020-06-05 | 青岛科技大学 | Preparation method of thiazoline compound containing selenium |
| WO2020147861A1 (en) * | 2019-01-17 | 2020-07-23 | 五邑大学 | Electrochemical preparation method for β-trifluoromethylamide compound |
| CN113881956A (en) * | 2021-10-11 | 2022-01-04 | 青岛科技大学 | Preparation method of benzyl isocyanate compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020147861A1 (en) * | 2019-01-17 | 2020-07-23 | 五邑大学 | Electrochemical preparation method for β-trifluoromethylamide compound |
| CN111235596A (en) * | 2020-01-21 | 2020-06-05 | 青岛科技大学 | Preparation method of thiazoline compound containing selenium |
| CN113881956A (en) * | 2021-10-11 | 2022-01-04 | 青岛科技大学 | Preparation method of benzyl isocyanate compound |
Non-Patent Citations (1)
| Title |
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| 袁履冰: "《有机化学学习指南》", 辽宁科学技术出版社, pages: 196 * |
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