CN112759525A - Preparation method of 2-methoxy ethylamine - Google Patents
Preparation method of 2-methoxy ethylamine Download PDFInfo
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- CN112759525A CN112759525A CN202011471259.6A CN202011471259A CN112759525A CN 112759525 A CN112759525 A CN 112759525A CN 202011471259 A CN202011471259 A CN 202011471259A CN 112759525 A CN112759525 A CN 112759525A
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- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000007800 oxidant agent Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 230000001590 oxidative effect Effects 0.000 claims abstract description 10
- WBTKTHOYLAMNGN-UHFFFAOYSA-N 1,3-bis(2-methoxyethyl)thiourea Chemical compound COCCNC(=S)NCCOC WBTKTHOYLAMNGN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 4
- 239000007858 starting material Substances 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 4
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 238000012216 screening Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- YSEFYOVWKJXNCH-UHFFFAOYSA-N 2-methoxyacetaldehyde Chemical compound COCC=O YSEFYOVWKJXNCH-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229940124149 Tankyrase inhibitor Drugs 0.000 description 1
- 150000004705 aldimines Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- -1 tert-Butanol peroxide Chemical class 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
Abstract
The invention relates to a preparation method of 2-methoxy ethylamine in the technical field of organic synthesis chemical industry, which takes N, N' -bis (2-methoxy ethyl) thiourea as a starting material, dissolves in a solvent, and prepares the 2-methoxy ethylamine through oxidation reaction in the presence of an oxidant. The method provided by the invention has the advantages of short steps, mild conditions and high product yield, and provides a universal new method for preparing 2-methoxy ethylamine.
Description
Technical Field
The invention belongs to the technical field of organic synthesis chemical industry, and particularly relates to a novel synthesis method of 2-methoxyethylamine.
Background
2-methoxy ethylamine (formula I) is an important chemical raw material, has good nucleophilic property and active chemical property, and is widely used in the industries of chemical pharmacy, high molecular materials, flame retardants, metal ligands, fine chemicals and the like. For example, 2-methoxyethylamine can be used for synthesizing a tankyrase inhibitor (formula III) with anticancer activity, preparing a metal ligand (formula IV) with good catalytic action, synthesizing a functional material intermediate (formula VI) with good flame retardant action and the like.
At present, the preparation methods of 2-methoxyethylamine reported in the literature mainly include the following methods:
(1) in 1951, James et al used the alkaline hydrolysis of Gabriel intermediate (2-methoxy-1-phthalimide) to prepare 2-methoxyethylamine. The method has low atom economy, is easy to generate a large amount of waste residues and has great influence on the environment. Several years later, Harder et al developed the use of boron trifluoride to catalyze the reaction of cycloaminoethane with methanol to produce 2-methoxyethylamine. Compared with the James method, the method is simple to operate, has small influence on the environment, and is difficult to obtain and store raw materials. At present, the method for industrially producing the 2-methoxy ethylamine is mainly prepared by dehydrating ethylene glycol monomethyl ether and ammonia at high temperature under the catalysis of nickel or alumina, but has low reaction yield of only 6 to 17 percent and higher requirement on reaction equipment.
(2) David Milstein et al, in toluene solution, using ruthenium (Ru) metal ligand to catalytically oxidize 2-methoxyethanol to form 2-methoxyacetaldehyde and form imine intermediate with ammonia, followed by ligand insertion and ligand exchange reaction to prepare 2-methoxyethylamine; the reaction is simple to operate and has high yield of 94%, but expensive metal Ru is needed to prepare the ligand, the cost is high, and the industrial production is not easy to realize.
(3) In patent CN 103936599a, ethanolamine and benzaldehyde are used as reaction raw materials, and are heated and refluxed in toluene to generate aldimine intermediate, which is then methylated under alkaline condition, deprotected and alkalinized, and then rectified to obtain pure 2-methoxyethylamine, wherein the reaction formula is as follows:
the reaction yield is high and is 84%, but the reaction route is complicated, sodium hydroxide is needed, and the reaction equipment is corroded to a certain extent.
Disclosure of Invention
In order to overcome the defects of the method, the invention provides the preparation method of the 2-methoxy ethylamine, so that the reaction step is short, the condition is mild, the cost is low, and the yield can reach more than 80%.
Therefore, the technical scheme provided by the invention is as follows: a preparation method of 2-methoxyethylamine uses N, N' -bis (2-methoxyethyl) thiourea (formula II) as a starting material, is dissolved in a solvent, and is subjected to oxidation reaction in the presence of an oxidant to prepare the 2-methoxyethylamine, wherein the reaction formula is as follows:
the selected oxidants in the reaction are tert-butyl peroxide, hydrogen peroxide and potassium persulfate (K)2S2O8) Sodium persulfate (Na)2S2O8) One kind of (1).
The oxidant is preferably potassium persulfate, and the dosage molar ratio of the potassium persulfate to the N, N' -bis (2-methoxyethyl) thiourea is (1-4): 1. the optimal dosage is that the molar ratio of the potassium persulfate to the N, N' -bis (2-methoxyethyl) thiourea is 3: 1.
the solvent is selected from one of ethanol, acetonitrile, dichloromethane, water and acetonitrile/water. Preferably, the solvent is a mixed solution of acetonitrile and water, and the volume ratio of acetonitrile to water is 1: (2.8-3.2), the volume ratio of acetonitrile to water is optimally 1:3.
the reaction temperature is 60-90 deg.c, preferably 80 deg.c, and the reaction time is 5-7 hr.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention provides a new route for synthesizing 2-methoxy ethylamine, which takes N, N' -bis (2-methoxy ethyl) thiourea as a raw material to prepare the 2-methoxy ethylamine through oxidation reaction.
(2) The preparation method is simple in preparation route, and the reaction solvent meets the requirement of green chemistry.
(3) The route provided by the invention has the advantages of mild reaction conditions, simple operation and good popularization and application values.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of a target compound;
FIG. 2 shows nuclear magnetic carbon spectra of the target compound.
Detailed Description
The present invention will be further described with reference to the following embodiments.
Analytical instrumentation and equipment used in the examples: nuclear magnetic resonance apparatus (AVANCE DMXIII 400M, Bruker).
Example 1: preparation of 2-methoxyethylamine
N, N' -bis (2-methoxyethyl) thiourea (19.2g, 0.1mol), 40ml acetonitrile, 120ml water, potassium persulfate (81g,0.3mol) were sequentially added to a 250ml round-bottom flask, and heated under reflux at 80 ℃ for 6 hours (GC tracing the progress of the reaction); the reaction formula is as follows:
after the reaction is finished, evaporating acetonitrile; cooling to room temperature, adding 100ml purified water, extracting with dichloromethane (40ml × 3), separating layers, drying the organic phase with anhydrous sodium sulfate, and concentrating to obtain crude product; the pure product 12.525g was obtained by distillation purification (87-90 ℃ fraction collected) with a yield of 83.5%.
Nuclear magnetic hydrogen spectrum and nuclear magnetic carbon of productThe spectral data are as follows:1H NMR(400MHz,CDCl3)δ3.38(t,J＝5.2Hz,2H)，3.34(s,3H),2.82(t, J＝5.2Hz,2H),1.56(s,2H).
13C NMR(100MHz,CDCl3)δ77.03,58.91,41.94.
the structural formula of the product is shown as the following formula I:
example 2: screening of oxidizing Agents
The experimental conditions and the charge amount in this example were the same as in example 1, and different oxidizing agents (3 times (molar ratio) of the raw material II) were selected for the experiment, and the specific conditions and charge amounts are shown in table 1:
TABLE 1
| Oxidizing agent | Yield of | |
| 1 | tert-Butanol peroxide | 46.2％ |
| 2 | Hydrogen peroxide solution | 13.5％ |
| 3 | Potassium persulfate | 83.5％ |
| 4 | Sodium persulfate | 78.3％ |
As can be seen from table 1, when hydrogen peroxide was selected as the oxidant, the reaction yield was the lowest, only 13.5%, when sodium persulfate was selected as the oxidant, the reaction yield was 78.3%, and when potassium persulfate was selected as the oxidant, the reaction yield was the highest, 83.5%; in summary, potassium persulfate is preferred as the reaction oxidant in the present invention.
Example 3: potassium persulfate (K)2S2O8) Screening of dosage
The experimental conditions and the amount of the feed in this example were the same as in example 1, and different dosages of K were selected2S2O8Experiments were performed as shown in table 2:
TABLE 2
| Dosage (mol) | Yield of | |
| 1 | 0.1 | 58.5％ |
| 2 | 0.2 | 71.3％ |
| 3 | 0.3 | 83.5％ |
| 4 | 0.4 | 84.0％ |
As can be seen from Table 2, when the amount of potassium persulfate was 0.1mol, the reaction yield was only 58.5%; when the amount is 0.3mol, the reaction yield is 83.5%, however, the reaction yield is not obviously improved by continuously increasing the amount of potassium persulfate; in conclusion, the invention selects 0.3mol of potassium persulfate to be optimal.
Example 4: screening of solvents
The experimental conditions and the charge amount of the present example were the same as those of example 1, and different reaction solvents were selected for the experiment, as shown in table 3:
TABLE 3
| Solvent(s) | Yield of | |
| 1 | Ethanol | 68.0％ |
| 2 | Acetonitrile | 46.2％ |
| 3 | Methylene dichloride | 23.5％ |
| 4 | Acetonitrile/water | 83.5％ |
| 5 | Water (W) | 76.5％ |
As can be seen from table 3, the reaction yield was the lowest when dichloromethane was selected as the solvent and was only 23.5%, while the reaction yield was 76.5% when water was selected as the solvent, and the reaction yield was the highest when a mixed solvent of acetonitrile and water was selected and was 83.5%; in summary, in the present invention, a mixed solution of acetonitrile and water is preferred as the reaction solvent.
Example 5: proportional screening of mixed solvent
The experimental conditions and the charge amount in this example were the same as those in example 1, and the experiment was carried out by selecting different solvent mixing ratios, as shown in table 4:
TABLE 4
| Acetonitrile: water (W) | Yield of | |
| 1 | 1:1 | 65.2％ |
| 2 | 1:2 | 73.7％ |
| 3 | 1:2.5 | 76.8％ |
| 4 | 1:2.8 | 83.3％ |
| 5 | 1:3 | 83.5％ |
| 6 | 1:3.2 | 83.5％ |
| 7 | 1:4 | 83.6％ |
| 8 | 1:5 | 83.5％ |
As can be seen from table 4, when the mixing ratio of acetonitrile and water is 1:1, the reaction yield is the lowest, only 65.2%, and when the mixing ratio of acetonitrile and water is 1:2, the reaction yield is 73.7%, when the mixing ratio of acetonitrile and water is 1:2.8, the reaction yield is 83.3%, when the mixing ratio of acetonitrile and water is 1:3, 1:3.2, the reaction yield is the highest, 83.5%, however, when the amount of water is continuously increased, the reaction yield is not significantly improved; in summary, the invention selects the mixing ratio of acetonitrile and water as 1: (2.8-3.2), preferably 1:3.
Example 6: screening of reaction temperature
The experimental conditions and the charge amount in this example were the same as those in example 1, and different reaction temperatures were selected for the experiment, as shown in table 5:
TABLE 5
| Temperature of | Yield of | |
| 1 | 60 | 55.3％ |
| 2 | 70 | 71.5％ |
| 3 | 80 | 83.5％ |
| 4 | 90 | 81.0％ |
As can be seen from Table 5, the reaction yield was the lowest at 60 ℃ and was only 55.3%, the reaction yield increased significantly with the increase of the reaction temperature, and the reaction yield was the highest at 83.5% when the selection reaction temperature was 80 ℃, but the reaction yield decreased with the continued increase of the temperature; in summary, the reaction temperature is 80 ℃.
The present invention is not limited to the above-mentioned embodiments, and based on the technical solutions disclosed in the present invention, those skilled in the art can make some substitutions and modifications to some technical features without creative efforts according to the disclosed technical contents, and these substitutions and modifications are all within the protection scope of the present invention.
Claims (9)
1. A preparation method of 2-methoxy ethylamine is characterized by comprising the following steps: dissolving N, N' -bis (2-methoxyethyl) thiourea as a starting material in a solvent, and preparing 2-methoxyethylamine through an oxidation reaction in the presence of an oxidant, wherein the reaction formula is as follows:
2. the method for preparing 2-methoxyethylamine according to claim 1, wherein: the oxidant selected in the reaction is one of tert-butyl peroxide, hydrogen peroxide, potassium persulfate and sodium persulfate.
3. The method for preparing 2-methoxyethylamine according to claim 2, wherein: the oxidant is potassium persulfate, and the molar ratio of the potassium persulfate to the N, N' -bis (2-methoxyethyl) thiourea is (1-4): 1.
4. the preparation method of 2-methoxyethylamine according to claim 3, wherein the molar ratio of the potassium persulfate to the N, N' -bis (2-methoxyethyl) thiourea is 3: 1.
5. a process for the preparation of a 2-methoxyethylamine according to any one of claims 1 to 4, wherein the solvent is selected from the group consisting of ethanol, acetonitrile, dichloromethane, water, acetonitrile/water.
6. The method for preparing 2-methoxyethylamine according to claim 5, wherein the solvent is a mixture of acetonitrile and water, and the volume ratio of acetonitrile to water is 1: (2.8-3.2).
7. The preparation method of 2-methoxyethylamine according to claim 6, wherein the volume ratio of acetonitrile to water is 1:3.
8. the process for preparing 2-methoxyethylamine according to any one of claims 1, 2, 3, 4, 6 and 7, wherein the reaction temperature is 60 ℃ to 90 ℃ and the reaction time is 5 to 7 hours.
9. The method of claim 8, wherein the reaction temperature is 80 ℃ and the reaction time is 6 hours.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113999125A (en) * | 2021-11-09 | 2022-02-01 | 苏州昊帆生物股份有限公司 | Preparation method of 2-methyl ethylamine |
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| WO2011106639A1 (en) * | 2010-02-25 | 2011-09-01 | Purdue Research Foundation | Psma binding ligand-linker conjugates and methods for using |
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| WO2016151508A1 (en) * | 2015-03-23 | 2016-09-29 | Sabic Global Technologies B.V. | Method and apparatus for the production of diaryl carbonate |
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| WO2011106639A1 (en) * | 2010-02-25 | 2011-09-01 | Purdue Research Foundation | Psma binding ligand-linker conjugates and methods for using |
| WO2012052996A2 (en) * | 2010-10-19 | 2012-04-26 | Yeda Research And Development Co. Ltd. | Novel ruthenium complexes and their uses in processes for formation and/or hydrogenation of esters, amides and derivatives thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113999125A (en) * | 2021-11-09 | 2022-02-01 | 苏州昊帆生物股份有限公司 | Preparation method of 2-methyl ethylamine |
| CN113999125B (en) * | 2021-11-09 | 2024-03-05 | 苏州昊帆生物股份有限公司 | Preparation method of 2-methoxyethylamine |
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