CN109557200A - A method of use gas chromatography monitoring methoxyl group oxalacetic acid methyl ethyl ester decarbonylation for methoxy propyl diacid methyl ethyl ester reaction end - Google Patents
A method of use gas chromatography monitoring methoxyl group oxalacetic acid methyl ethyl ester decarbonylation for methoxy propyl diacid methyl ethyl ester reaction end Download PDFInfo
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Abstract
Use gas chromatography monitoring methoxyl group oxalacetic acid methyl ethyl ester decarbonylation for the method for methoxy propyl diacid methyl ethyl ester reaction end the invention discloses a kind of, for analyzing methoxy propyl diacid methyl ethyl ester reaction end.
Description
Technical field
The present invention relates to a kind of monitoring methoxy propyl diacid methyl ethyl esters to prepare reaction method, specifically a kind of to use gas phase color
Spectrometry monitors the method that methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is methoxy propyl diacid methyl ethyl ester reaction end.
Background technique
Methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is that the reaction of methoxy propyl diacid methyl ethyl ester is synthesis sulfamethoxine intermediate two
The key reaction of chlorine object.Sulfamethoxine (Sulfadoxine) also known as sulfadoxine, the entitled 4- (P-aminobenzene-sulfonamide of chemistry
Base) -5,6- dimethoxypyridin, No. CAS is 2447-57-6, and chemical structural formula is as follows:
Sulfamethoxine can be clinically used for treating general inflammation, such as infection of the upper respiratory tract tonsillitis, bacillary dysentery enteritis, skin
Skin infection etc. can also treat pulmonary tuberculosis, scrofula with its other medicine compatibility；It also has certain curative effect to (crazy) disease of leprosy, also can
Malaria is treated, the prophylactic of rheumatism can be additionally made.When for such use, sulfamethoxine has curative effect long, and toxicity is low
The characteristics of.It experienced the research and development of several generations, sulfamethoxine intermediate methoxy propyl diacid methyl ethyl ester production technology is gradually steady
Fixed, reaction equation is as follows:
Methoxy propyl diacid methyl ethyl ester is the important intermediate for preparing sulfamethoxine, and yield directly affects sulfamethoxine
Yield and cost.CN103910629A, CN103910630 disclose the preparation method of methoxy propyl diacid methyl ethyl ester, specially
Methoxy menthyl acetate and diethy-aceto oxalate 50-60 DEG C of conditioned response under the action of solid-state sodium methoxide produce methoxyl group grass second
Sour methyl ethyl ester, then decarbonylation aftercut obtain methoxy propyl diacid methyl ethyl ester；However methoxyl group oxalacetic acid methyl ethyl ester decarbonylation generates first
The process of oxygroup malonic acid methyl ethyl ester does not have effective monitoring means, is easy to cause decarbonylation time too short decarbonylation incomplete, or
Decarbonylation overlong time generates high-boiling-point impurity, causes intermediate methoxy propyl diacid methyl ethyl ester purity low, yield is low, is unfavorable for vehicle
Between production technology even running.
Summary of the invention
It is provided the purpose of the invention is to overcome the deficiencies in the prior art a kind of using gas chromatography monitoring methoxy
Base oxalacetic acid methyl ethyl ester decarbonylation is the method for methoxy propyl diacid methyl ethyl ester reaction end.This method is surveyed using gas chromatography
It is fixed, favorable reproducibility, high sensitivity, the features such as detection is accurate, specificity is strong, easy to operate, most critical be can grasp in time it is de-
Carbonyl situation improves the purity and yield of intermediate methoxy propyl diacid methyl ethyl ester, is finally reached the steady fortune of plant manufacturing process
Row.
To achieve the above object, the present invention adopts the following technical scheme: it is a kind of using gas chromatography monitoring methoxyl group grass
Acetic acid methyl ethyl ester decarbonylation is the method for methoxy propyl diacid methyl ethyl ester reaction end, and described method includes following steps:
(1) chromatographic condition:
Gas chromatograph is that a kind of more mixtures separate, analyze tool, it is using gas as mobile phase, using punching
Wash the Column chromatography techniques of method.When the analysis substance of multiple groups part enters chromatographic column, due to the gas phase of each component in the chromatography column
Distribution coefficient between fixer liquid phase is different, therefore each component is also just different in the speed of service of chromatographic column, by certain
After column length, sequentially leaves chromatographic column and enter detector, electric signal is converted to after detecting and is sent to data processing stations, thus complete
At the qualitative and quantitative analysis to measured matter.Group is measured after distributing chromatographic column into detector, and common detector has
Hydrogen flame detector (FID), electron capture detector (ECD), flame photometric detector (FPD) and thermal conductivity detector (TCD) (TCD) etc..
This method uses hydrogen flame detector (FID).
Principle: the absorption or dissolution, desorption or parsing between gas-solid or gas-liquid two-phase are carried out using tested component and stationary phase
Etc. physicochemical properties difference, in column formed component migration velocity difference and separated
Capillary chromatographic column: the capillary column with fixer similar in (5%- phenyl)-methyl polysiloxane or polarity is
Chromatographic column 30m × 0.32mm × 1.0 μm
Carrier gas: nitrogen
Column temperature: 120 DEG C of initial temperature, 240 DEG C is risen to 10 DEG C/min, is kept for 20 minutes.
Gasify room temperature: 250 DEG C
Detector (FID) temperature: 280 DEG C
Sample volume: 0.1 μ l
Measuring method precision measures test solution and each 0.1 μ l of reference substance solution, is injected separately into gas chromatograph, records color
Spectrogram.It is calculated as follows with the content (C) of areas of peak normalization method, each peak:
In formula: each peak peak area in A- chromatogram；
The summation of each peak area in chromatogram.
(2) methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is the preparation of test solution before methoxy propyl diacid methyl ethyl ester reacts；
(3) methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is that methoxy propyl diacid methyl ethyl ester reacts matching for 2 hours test solutions
System；
(4) methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is that methoxy propyl diacid methyl ethyl ester reacts matching for 4 hours test solutions
System；
(5) measuring method:
Taking methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is test solution before methoxy propyl diacid methyl ethyl ester reacts, and injects gas phase
Chromatograph, records map, and area normalization method calculates the content and record methoxyl group oxalacetic acid first of methoxyl group oxalacetic acid methyl ethyl ester
Ethyl ester retention time；Taking methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is that methoxy propyl diacid methyl ethyl ester reacts 2 hours test solutions,
Gas chromatograph is injected, map is recorded, area normalization method calculates the content and record methoxyl group of methoxyl group oxalacetic acid methyl ethyl ester
Oxalacetic acid methyl ethyl ester retention time is completed as the content of methoxyl group oxalacetic acid methyl ethyl ester is considered as reaction less than 1.00%, is greater than
Equal to 1.00%, the reaction was continued 2 hours；Taking methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is that methoxy propyl diacid methyl ethyl ester reacts 4 hours
Test solution, inject gas chromatograph, record map, area normalization method calculate methoxyl group oxalacetic acid methyl ethyl ester content and
Methoxyl group oxalacetic acid methyl ethyl ester retention time is recorded, as the content of methoxyl group oxalacetic acid methyl ethyl ester is considered as reaction less than 1.00%
Complete, be more than or equal to that 1.00% the reaction was continued 2 hours, and so on until the reaction is complete until.
The specification of the chromatographic column be with (5%- phenyl)-methyl polysiloxane or polarity it is close be fixer capillary
Column is chromatographic column (30m × 0.32mm × 1.0um) (such as HP-5, DB-5, DP-5, SE-54, SPB-5, GC-5,007-2, RSL-
200 equal capillary columns).
The invention is characterized by its reaction solution detection method.The basic principle of the detection method is to utilize gas-chromatography
Method area normalization method calculates the first and second ester content of methoxyl group oxalacetic acid.
It is a kind of to use gas chromatography monitoring methoxyl group oxalacetic acid methyl ethyl ester decarbonylation for the reaction of methoxy propyl diacid methyl ethyl ester
The method of terminal compared with prior art, has the characteristics that reproducibility, sensitivity, accuracy can meet the requirements, will answer extensively
For organic synthesis monitoring field.
The essential structure of gas chromatograph has two parts, i.e. analytical unit and display unit.The former mainly include gas source and
Control metering device, sampling device, thermostat and chromatographic column.The latter mainly includes comparator and automatic recording instrument.Chromatographic column (packet
Include stationary phase) and comparator be the core component of gas chromatograph.
(1) gas circuit in air-channel system gas chromatograph is the pipeline liquid injecting device system of a carrier gas continuous operation.Entire gas
Road system requirements carrier gas is pure, good leak tightness, flow speed stability and flow velocity measurement are accurate.
(2) sampling system sample introduction is exactly that gas or fluid sample at the uniform velocity and are quantitatively added to chromatographic column upper end.
(3) core of separation system separation system is chromatographic column, its effect is that multicomponent sample is separated into single group
Point.Chromatographic column is divided into two class of packed column and capillary column.
(4) effect of detection system detector is being converted by the sample component of chromatography post separation according to its characteristic and content
It is amplified at electric signal, chromatogram is recorded as by recorder.
(5) gas chromatograph mainly uses chromatographic data processor in recent years for signal record or computer data processing system.
The printable record chromatogram of chromatographic data processor, and can print that treated as a result, as retained in same recording sheet
Time, tested constituent mass score etc..
(6) temperature control system is gas chromatograph for controlling and measuring chromatographic column, detector, gasification room temperature
Important component.Gas chromatograph is divided into two classes: one kind is gas-solid chromatograph instrument, and another kind of is gas-liquid partition chromatography instrument.This two
The separated stationary phase of class chromatograph is different, but the structure of instrument is general.
Detailed description of the invention
The following describes the present invention in detail with reference to the accompanying drawings and embodiments.
Fig. 1 is that methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is test sample map before methoxy propyl diacid methyl ethyl ester reacts.
Fig. 2 is that methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is that methoxy propyl diacid methyl ethyl ester reacts 2 hours test sample maps.
Fig. 3 is that methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is that methoxy propyl diacid methyl ethyl ester reacts 4 hours test sample maps.
Specific embodiment
The present invention will be further explained with reference to the examples below, and embodiment helps to more fully understand the present invention, but
The present invention is not limited only to following embodiments.
Embodiment one
1, chromatographic condition:
Using (5%- phenyl)-methyl polysiloxane or polarity it is close be fixer capillary column as chromatographic column (30m ×
0.32mm × 1.0um), initial temperature is 120 DEG C, is warming up to 240 DEG C with 10 DEG C of rate per minute, maintains 20 minutes；Sample introduction
250 DEG C of temperature of mouth；280 DEG C of detector temperature, detector is flame ionization ditector.
Measuring method precision measures test solution and each 0.1 μ l of reference substance solution, is injected separately into gas chromatograph, records color
Spectrogram.By percent area method with methoxy propyl diacid methyl ethyl ester in calculated by peak area test solution or methoxyl group oxalacetic acid first and second
The content at ester peak.
2, the preparation of related solution:
2.1 methoxyl group oxalacetic acid methyl ethyl ester decarbonylations are the preparation of test solution before methoxy propyl diacid methyl ethyl ester reacts；
2.2 methoxyl group oxalacetic acid methyl ethyl ester decarbonylations are that methoxy propyl diacid methyl ethyl ester reacts matching for 2 hours test solutions
System；
2.3 methoxyl group oxalacetic acid methyl ethyl ester decarbonylations are that methoxy propyl diacid methyl ethyl ester reacts matching for 4 hours test solutions
System；
3, measuring method:
Taking methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is test solution before methoxy propyl diacid methyl ethyl ester reacts, and injects gas phase
Chromatograph, records map, and area normalization method calculates the content and record methoxyl group oxalacetic acid first of methoxyl group oxalacetic acid methyl ethyl ester
Ethyl ester retention time；Taking methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is that methoxy propyl diacid methyl ethyl ester reacts 2 hours test solutions,
Gas chromatograph is injected, map is recorded, area normalization method calculates the content and record methoxyl group of methoxyl group oxalacetic acid methyl ethyl ester
Oxalacetic acid methyl ethyl ester retention time is completed as the content of methoxyl group oxalacetic acid methyl ethyl ester is considered as reaction less than 1.00%, is greater than
Equal to 1.00%, the reaction was continued 2 hours；Taking methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is that methoxy propyl diacid methyl ethyl ester reacts 4 hours
Test solution, inject gas chromatograph, record map, area normalization method calculate methoxyl group oxalacetic acid methyl ethyl ester content and
Methoxyl group oxalacetic acid methyl ethyl ester retention time is recorded, as the content of methoxyl group oxalacetic acid methyl ethyl ester is considered as reaction less than 1.00%
Complete, be more than or equal to that 1.00% the reaction was continued 2 hours, and so on until the reaction is complete until.
Inspection result
Test sample (before decarbonylation) map: such as Fig. 1, the first and second ester content of methoxyl group oxalacetic acid is peak RT6.5min and peak
The summation of RT7.4min content, it is 86.99% that area normalization method, which calculates the first and second ester content of methoxyl group oxalacetic acid,.
Test sample (decarbonylation 2 hours) map such as Fig. 2: the first and second ester content of methoxyl group oxalacetic acid is peak RT6.6min and peak
The summation of RT7.5min content, area normalization method calculate the first and second ester content of methoxyl group oxalacetic acid be 47.23%；Methoxy propyl
The first and second ester content of diacid is the summation of peak RT4.7min and peak RT5.5min content, and area normalization method calculates to obtain methoxy propyl two
Sour first and second ester contents are 34.35%.It follows that the first and second ester content of methoxyl group oxalacetic acid is greater than 1%, need to continue decarbonylation anti-
It answers.
Test sample (decarbonylation 4 hours) map such as Fig. 3: the first and second ester content of methoxyl group oxalacetic acid is the content of peak RT7.7min,
Area normalization method calculate the first and second ester content of methoxyl group oxalacetic acid be 0.13%, less than 1%, decarbonylation reaction is complete, can stop
Reaction.
Claims (3)
1. a kind of use gas chromatography monitoring methoxyl group oxalacetic acid methyl ethyl ester decarbonylation to react eventually for methoxy propyl diacid methyl ethyl ester
The method of point includes the following steps:
(1) chromatographic condition: using (5%- phenyl)-methyl polysiloxane or polarity, the close capillary column for being fixer is chromatographic column
(30m × 0.32mm × 1.0um), initial temperature are 120 DEG C, are warming up to 240 DEG C with 10 DEG C of rate per minute, maintain 20 points
Clock；250 DEG C of injector temperature；280 DEG C of detector temperature, detector is flame ionization ditector；
Measuring method precision measures test solution and each 0.1 μ l of reference substance solution, is injected separately into gas chromatograph, records chromatography
Figure.By percent area method with the content at methoxy propyl diacid methyl ethyl ester peak in calculated by peak area test solution；
(2) methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is the preparation of test solution before methoxy propyl diacid methyl ethyl ester reacts；
(3) methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is the preparation that methoxy propyl diacid methyl ethyl ester reacts 2 hours test solutions；
(4) methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is the preparation that methoxy propyl diacid methyl ethyl ester reacts 4 hours test solutions；
(5) measuring method:
Taking methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is test solution before methoxy propyl diacid methyl ethyl ester reacts, and injects gas-chromatography
Instrument, records map, and area normalization method calculates the content and record methoxyl group oxalacetic acid methyl ethyl ester of methoxyl group oxalacetic acid methyl ethyl ester
Retention time；Taking methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is that methoxy propyl diacid methyl ethyl ester reacts 2 hours test solutions, injection
Gas chromatograph, records map, and area normalization method calculates the content and record methoxyl group grass second of methoxyl group oxalacetic acid methyl ethyl ester
Sour methyl ethyl ester retention time is completed as the content of methoxyl group oxalacetic acid methyl ethyl ester is considered as reaction less than 1.00%, is more than or equal to
1.00% the reaction was continued 2 hours；Taking methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is that methoxy propyl diacid methyl ethyl ester reacts 4 hours for examination
Product solution injects gas chromatograph, records map, and area normalization method calculates the content and record of methoxyl group oxalacetic acid methyl ethyl ester
Methoxyl group oxalacetic acid methyl ethyl ester retention time has been reacted as the content of methoxyl group oxalacetic acid methyl ethyl ester is considered as less than 1.00%
At, be more than or equal to that 1.00% the reaction was continued 2 hours, and so on until the reaction is complete until.
2. it is according to claim 1 it is a kind of use gas chromatography monitoring methoxyl group oxalacetic acid methyl ethyl ester decarbonylation for methoxyl group
The method of malonic acid methyl ethyl ester reaction end, it is characterised in that the specification of the chromatographic column is with (5%- phenyl)-methyl polysilicon
Oxygen alkane or polarity it is close be the capillary column of fixer be chromatographic column 30m × 0.32mm × 1.0um (such as HP-5, DB-5, DP-
5, the capillary columns such as SE-54, SPB-5, GC-5,007-2, RSL-200).
3. it is according to claim 1 it is a kind of use gas chromatography monitoring methoxyl group oxalacetic acid methyl ethyl ester decarbonylation for methoxyl group
The method of malonic acid methyl ethyl ester reaction end, which is characterized in that the methoxyl group oxalacetic acid methyl ethyl ester decarbonylation is methoxy propyl two
Test solution before sour methyl ethyl ester reacts, 0.1 μ l of direct injected after being sampled with sampler；The methoxyl group oxalacetic acid methyl ethyl ester is de-
Carbonyl is test solution after the reaction of methoxy propyl diacid methyl ethyl ester, 0.1 μ l of direct injected after being sampled with sampler.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102304094A (en) * | 2011-09-23 | 2012-01-04 | 常熟市南湖实业化工有限公司 | Preparation method of sulfadoxine and intermediate thereof |
| WO2012155108A1 (en) * | 2011-05-11 | 2012-11-15 | Ironwood Pharmaceuticals, Inc. | Treatments for disorders using guanylate cyclase c agonists |
| CN103910629A (en) * | 2014-03-10 | 2014-07-09 | 常熟市南湖实业化工有限公司 | Method used for smooth and steady preparation of 2-methoxypropandioic acid ethyl methyl ester |
| CN104447327A (en) * | 2014-12-13 | 2015-03-25 | 常熟市金申医化制品有限责任公司 | Preparation method of methyl ethyl methoxymalonate |
| CN108658871A (en) * | 2018-06-19 | 2018-10-16 | 张家港威胜生物医药有限公司 | The preparation method of sulfamethoxine intermediate 4,6- dichloro-5-methoxy pyrimidines |
-
2018
- 2018-11-23 CN CN201811404726.6A patent/CN109557200A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012155108A1 (en) * | 2011-05-11 | 2012-11-15 | Ironwood Pharmaceuticals, Inc. | Treatments for disorders using guanylate cyclase c agonists |
| CN102304094A (en) * | 2011-09-23 | 2012-01-04 | 常熟市南湖实业化工有限公司 | Preparation method of sulfadoxine and intermediate thereof |
| CN103910629A (en) * | 2014-03-10 | 2014-07-09 | 常熟市南湖实业化工有限公司 | Method used for smooth and steady preparation of 2-methoxypropandioic acid ethyl methyl ester |
| CN104447327A (en) * | 2014-12-13 | 2015-03-25 | 常熟市金申医化制品有限责任公司 | Preparation method of methyl ethyl methoxymalonate |
| CN108658871A (en) * | 2018-06-19 | 2018-10-16 | 张家港威胜生物医药有限公司 | The preparation method of sulfamethoxine intermediate 4,6- dichloro-5-methoxy pyrimidines |
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