CN107082755B - A kind of preparation method of diethylamino ethanethiol impurity - Google Patents
A kind of preparation method of diethylamino ethanethiol impurity Download PDFInfo
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- CN107082755B CN107082755B CN201710125034.7A CN201710125034A CN107082755B CN 107082755 B CN107082755 B CN 107082755B CN 201710125034 A CN201710125034 A CN 201710125034A CN 107082755 B CN107082755 B CN 107082755B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The present invention relates to a kind of preparation method of diethylamino ethanethiol impurity, the preparation method of the impurity B be 1:1 ~ 1:1.5 by molar ratio diethylamino ethanethiol and thiirane be added in petroleum ether, maintain the temperature between -3 ~ -8 DEG C, stir 3-15h；It is that the impurity B of 1:1 ~ 1.5 and thiirane are added in petroleum ether that the preparation method of the impurity C, which is by molar ratio, is maintained the temperature between -2 ~ -8 DEG C, and 3-15h is stirred；It is that the impurity C of 1:1 ~ 1.5 and thiirane are added in petroleum ether that the preparation method of the impurity D, which is by molar ratio, is maintained the temperature between -2 ~ -8 DEG C, and 3-15h is stirred；The present invention can be used as impurity reference substance, be conducive to the quality control of diethylamino ethanethiol in production process.
Description
Technical field
The present invention relates to drug fields, and in particular to a kind of preparation method of diethylamino ethanethiol impurity.
Background technique
Diethylamino ethanethiol is the important intermediate for producing Tiamulin, and Tiamulin is that one kind is exhaled for preventing and treating poultry
Desorption system disease and the dedicated antibiotic of diterpene alkenes livestock and poultry for promoting growth of animal.Due to diethylamino ethanethiol molecular structure
Particularity inevitably generates by-product in process of production, studies its impurity for producing high-purity diethylamino ethanethiol
It is most important.Structural formula is as follows:
In order to preferably control the quality of diethylamino ethanethiol, need to produce the impurity for obtaining diethylamino ethanethiol,
As impurity reference substance, reference can be provided for the selection of process conditions, be conducive to diethylamino ethanethiol in production process
Quality control.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of diethylamino ethanethiol impurity, impurity purity is high obtained,
Conversion ratio is good.
To achieve the above object, the impurity includes impurity B, impurity C and impurity D；
The impurity B is, it is 1:1 ~ 1:1.5 that preparation method, which is by molar ratio,
Diethylamino ethanethiol and thiirane be added in petroleum ether, the amount that petroleum ether is added is diethylamino ethanethiol quality
200%, it keeps reaction temperature between -3 ~ -8 DEG C, stirs 3-15h；
The impurity C is, preparation method be by molar ratio 1:1 ~
1.5 impurity B and thiirane is added in petroleum ether, and the amount that petroleum ether is added is the 200% of the impurity B quality, is protected
Reaction temperature is held between -2 ~ -8 DEG C, stirs 3-15h；
The impurity D is,, preparation method is that will rub
, than being added in petroleum ether for the impurity C and thiirane of 1:1 ~ 1.5, the amount that petroleum ether is added is the impurity C matter for you
The 200% of amount keeps reaction temperature between -2 ~ -8 DEG C, stirs 3-15h.
Preferably: the reaction temperature of the impurity C is maintained at -3 DEG C.
Preferably: the reaction temperature of the impurity D is maintained at -3 DEG C.
Preferably: the reaction temperature of the impurity B is maintained at -5 DEG C.
Preferably: further including impurity A, the impurity A is, preparation side
Method are as follows: aoxidize diethylamino ethanethiol in oxygen, reaction temperature is 50-100 DEG C, and the molal quantity of the oxygen is at least two
The half of ethylamino ethyl mercaptan molal quantity reacts 0.8-2.5h.
Preferably: the reaction temperature is 65 DEG C.
Good effect of the present invention is as follows:
Preparation method of the present invention production is simple, at low cost, the purity is high of impurity A obtained, impurity B, impurity C and impurity D,
High conversion rate, effective acquisition of these impurity can be used as the impurity reference substance of diethylamino ethanethiol, be the selection of process conditions
Reference is provided, is conducive to the quality control of diethylamino ethanethiol in production process, for producing high-purity lignocaine second sulphur
Alcohol is most important.
Detailed description of the invention
Fig. 1 is the mass spectrogram of the embodiment of the present invention 1；
The mass spectrogram of Fig. 2 embodiment of the present invention 5；
Fig. 3 is 7 mass spectrogram of the embodiment of the present invention；
The mass spectrogram of Fig. 4 embodiment of the present invention 12.
Specific embodiment
It will make further narration in detail to the embodiment of the present invention below.
The proportion of each embodiment is as shown in table 1
The proportion of each embodiment of table 1
Embodiment 1
20g diethylamino ethanethiol is added in the four-hole bottle of 100mL, leads to oxygen 1.5h, lignocaine under the conditions of 50 DEG C
The molar ratio of ethyl mercaptan and oxygen is 1:0.5, obtains impurity A, finds after being detected using GC-MS, structure formula and structural formula of compound
It is consistent, the mass spectrogram of conversion ratio 91.3%, the impurity A of embodiment 1 is as shown in Figure 1.Reaction process are as follows:
Embodiment 2
20g diethylamino ethanethiol is added in the four-hole bottle of 100mL, leads to oxygen 2.5h, lignocaine under the conditions of 65 DEG C
The molar ratio of ethyl mercaptan and oxygen be 1:1, obtain impurity A, conversion ratio 92.1% is found after being detected using GC-MS, structure formula with
Structural formula of compound is consistent.
Embodiment 3
20g diethylamino ethanethiol is added in the four-hole bottle of 100mL, leads to oxygen 0.8h, lignocaine under the conditions of 100 DEG C
The molar ratio of ethyl mercaptan and oxygen be 1:10, obtain impurity A, conversion ratio 92.5% is found after being detected using GC-MS, structure formula with
Structural formula of compound is consistent.
Embodiment 4
In the four-hole bottle of 500mL, addition 66.58g diethylamino ethanethiol, 200mL petroleum ether, dripped in this system
Add the mixed solution of 30.06g thiirane and 100mL petroleum ether, the density of petroleum ether is 0.64-0.66 g/ cubic centimetres, dimension
Temperature is held at -5 DEG C, stirs 5h, reaction terminates, and decompression steams petroleum ether and obtains compound B 90.01g.Conversion ratio is 93.3%,
GC-MS detection, structural formula are consistent with structural formula of compound.Reaction process is as follows:
Embodiment 5
In the four-hole bottle of 500mL, addition 66.58g diethylamino ethanethiol, 200mL petroleum ether, dripped in this system
Add the mixed solution of 45.01g thiirane and 140mL petroleum ether, the density of petroleum ether is 0.64-0.66 g/ cubic centimetres, dimension
Temperature is held at -3 DEG C, stirs 3h, reaction terminates, and decompression steams petroleum ether and obtains compound B 88.78g.GC-MS detection, structure
Formula is consistent with structural formula of compound.Conversion ratio is 92.0%, and the mass spectrogram of the impurity B of embodiment 5 is as shown in Figure 2.
Embodiment 6
In the four-hole bottle of 500mL, 66.58g diethylamino ethanethiol is added, 200mL petroleum ether is added dropwise in this system
The mixed solution of 36.10g thiirane and 120mL petroleum ether, the density of petroleum ether are 0.64-0.66 g/ cubic centimetres, are maintained
Temperature stirs 15h at -8 DEG C, and reaction terminates, and decompression steams petroleum ether and obtains compound B 88.59g.Conversion ratio is 91.8%,
GC-MS detection, structural formula are consistent with structural formula of compound.
Embodiment 7
In the four-hole bottle of 250mL, 64.39g impurity B is added, 20.01g ring is added dropwise in 200mL petroleum ether in this system
The mixed solution of sulphur ethane and 60mL petroleum ether, the density of petroleum ether are 0.64-0.66 g/ cubic centimetres, maintain temperature -3
DEG C, 5h is stirred, reaction terminates, and decompression steams petroleum ether and obtains compound C 78.25g.GC-MS detection, structural formula and compound
Structural formula is consistent.Conversion ratio is 92.7%, and the mass spectrogram of the impurity C of embodiment 7 is as shown in Figure 3.
Embodiment 8
In the four-hole bottle of 250mL, addition 64.39g impurity B, 200mL petroleum ether, 30.03g ring is added dropwise in this system
The mixed solution of sulphur ethane and 90mL petroleum ether, the density of petroleum ether are 0.64-0.66 g/ cubic centimetres, maintain temperature -8
DEG C, 3h is stirred, reaction terminates, and decompression steams petroleum ether and obtains compound C 78.66g.Conversion ratio is 93.2%, GC-MS detection,
Structural formula is consistent with structural formula of compound.
Embodiment 9
In the four-hole bottle of 250mL, addition 64.39g impurity B, 200mL petroleum ether, 28.06g ring is added dropwise in this system
The mixed solution of sulphur ethane and 90mL petroleum ether, the density of petroleum ether are 0.64-0.66 g/ cubic centimetres, maintain temperature -2
DEG C, 15h is stirred, reaction terminates, and decompression steams petroleum ether and obtains compound C 79.09g.GC-MS detection, structural formula and compound
Structural formula is consistent.Conversion ratio is 93.7%,
Embodiment 10
In the four-hole bottle of 100mL, 63.29g impurity C, 200mL petroleum ether is added, 15.01g ring is added dropwise in this system
The mixed solution of sulphur ethane and 50mL petroleum ether, the density of petroleum ether are 0.64-0.66g/ cubic centimetres, maintain temperature -3
DEG C, 5h is stirred, reaction terminates, and decompression steams petroleum ether and obtains compound D75.54g.GC-MS detection, structural formula and compound knot
Structure formula is consistent.Conversion ratio is 91.1%, and reaction process is as follows:
Embodiment 11
In the four-hole bottle of 100mL, 63.29g impurity C, 200mL petroleum ether is added, 22.51g ring is added dropwise in this system
The mixed solution of sulphur ethane and 60mL petroleum ether, the density of petroleum ether are 0.64-0.66 g/ cubic centimetres, maintain temperature -8
DEG C, 15h is stirred, reaction terminates, and decompression steams petroleum ether and obtains compound D 76.98g.GC-MS detection, structural formula and compound
Structural formula is consistent.Conversion ratio is 91.9%,
Embodiment 12
In the four-hole bottle of 100mL, 63.29g impurity C, 200mL petroleum ether is added, the density of petroleum ether is 0.64-0.66
G/ cubic centimetres, the mixed solution of 21.01g thiirane and 60mL petroleum ether is added dropwise in this system, maintains temperature at -2 DEG C,
3h is stirred, reaction terminates, and decompression steams petroleum ether and obtains compound D 76.49g.GC-MS detection, structural formula and compound structure
Formula is consistent.Conversion ratio is 92.2%, and the mass spectrogram of the impurity D of embodiment 12 is as shown in Figure 4.
The foregoing description of the disclosed embodiments enables those skilled in the art to implement or use the present invention.
Various modifications to these embodiments will be readily apparent to those skilled in the art, as defined herein
General Principle can be realized in other embodiments in the case where not departing from the spirit or scope of the invention patent.Therefore, originally
Invention is not intended to be limited to the embodiments shown herein, and is to fit to and the principles and novel features disclosed herein
Consistent widest scope.
Claims (4)
1. a kind of preparation method of diethylamino ethanethiol impurity, it is characterised in that: the impurity includes impurity B, impurity C and miscellaneous
Matter D；
The impurity B is, preparation method be the two of 1:1 ~ 1:1.5 by molar ratio
Ethylamino ethyl mercaptan and thiirane are added in petroleum ether, and the amount that petroleum ether is added is diethylamino ethanethiol quality
200%, it keeps reaction temperature between -3 ~ -8 DEG C, stirs 3-15h；
The impurity C is, it is 1:1 ~ 1.5 that preparation method, which is by molar ratio,
The impurity B and thiirane are added in petroleum ether, and the amount that petroleum ether is added is the 200% of the impurity B quality, keep anti-
It answers temperature between -2 ~ -8 DEG C, stirs 3-15h；
The impurity D is,, preparation method is to be by molar ratio
The impurity C and thiirane of 1:1 ~ 1.5 are added in petroleum ether, and the amount that petroleum ether is added is the impurity C mass
200%, it keeps reaction temperature between -2 ~ -8 DEG C, stirs 3-15h.
2. a kind of preparation method of diethylamino ethanethiol impurity according to claim 1, it is characterised in that: the impurity
The reaction temperature of C is maintained at -3 DEG C.
3. a kind of preparation method of diethylamino ethanethiol impurity according to claim 1, it is characterised in that: the impurity
The reaction temperature of D is maintained at -3 DEG C.
4. a kind of preparation method of diethylamino ethanethiol impurity according to claim 1, it is characterised in that: the impurity
The reaction temperature of B is maintained at -5 DEG C.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104774164A (en) * | 2015-02-16 | 2015-07-15 | 张丽学 | Preparation process for 2-diethylaminoethanethiol |
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| JP3794650B2 (en) * | 1995-12-14 | 2006-07-05 | 住友精化株式会社 | Method for producing aliphatic mercapto compound having hydroxyl group |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104774164A (en) * | 2015-02-16 | 2015-07-15 | 张丽学 | Preparation process for 2-diethylaminoethanethiol |
Non-Patent Citations (2)
| Title |
|---|
| N,S Ligands for Preconcentration or Elimination of Heavy Metals. Synthesis and Characterisation of Aminoethanethiols and Aminoethanethiol-modified Silica Gel;Carole Bresson et al.;《 J. CHEM. RESEARCH》;19980101;第490页右栏scheme1 |
| Platinum phosphinothiolato hydride complexes:synthesis, structure and evaluation as tin-free hydroformylation catalysts;Julio Real et al.;《Dalton Trans》;20160203;第45卷;第3970页右栏最后1段 |
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Effective date of registration: 20190618 Address after: 071000 Pang Village, Yujiazhuang Township, Mancheng District, Baoding City, Hebei Province Patentee after: Baoding Jiahe Fine Chemical Co., Ltd. Address before: 050000 26 Yuxiang Street, Shijiazhuang City, Hebei Province Patentee before: Hebei University of Science and Technology |