CN105601544A - Synthesis method of 2-methoxyl-5-amino sulfanoylmethyl benzoate - Google Patents
Synthesis method of 2-methoxyl-5-amino sulfanoylmethyl benzoate Download PDFInfo
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- CN105601544A CN105601544A CN201511010527.3A CN201511010527A CN105601544A CN 105601544 A CN105601544 A CN 105601544A CN 201511010527 A CN201511010527 A CN 201511010527A CN 105601544 A CN105601544 A CN 105601544A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
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Abstract
The invention provides a synthesis method of 2-methoxyl-5-amino sulfanoyl methyl benzoate. The synthesis method comprises the following steps: adding 2-methoxyl-5-chloromethyl benzoate, amino sodium sulfinate, a solvent and a catalyst into a reaction device; controlling the temprature to be 40 DEG C to 65 DEG C to react for 8 to 16 hours; after the reaction is finished, adding active carbon for de-coloring; filtering to remove the active carbon, the catalyst and a byproduct sodium chloride; concentrating under reduced pressure a filtrate to obtain the 2-methoxyl-5-sulfamoyl methyl benzoate. The synthesis method of the 2-methoxyl-5-sulfamoyl methyl benzoate, provided by the invention, has the advantages of short original technological process, high yield and good quality, has no three wastes which pollute the environment, is very environmental friendly, and is suitable for large-scale industrial production.
Description
Technical field
The invention belongs to organic compound synthesis technical field, particularly, relate to a kind of synthetic method of 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters.
Background technology
2-methoxyl group-5-sulfamoylbenzoic acid methyl esters is the important intermediate of anti-antipsychotics Sulpiride and left-handed Sulpiride. As shown in Figure 1, it is synthetic all adopt both at home and abroad at present salicylic acid through methylating, chlorosulfonation, amination, esterification must this products, its process route is long, the quantity of three wastes that each step produces is large, especially high chemical oxygen demand (COD), high salt, high ammonia nitrogen, composite waste etc., intractability is large, and processing cost is high, has seriously restricted this product large-scale industrial production. The present invention adopts brand-new technique with line, adopt under a small amount of catalyst existence of amino sulfinic acid sodium and 2-methoxy-5-chlorobenzoic acid methyl esters, direct polycondensation and obtain this product, greatly shorten its synthetic route, overcome the large shortcoming of above-mentioned three wastes generation, in purge process, produce a small amount of active carbon residue, produce without other three wastes free from environmental pollution, and its quality and yield exceed existing technique indices.
Summary of the invention
Goal of the invention: for the deficiencies in the prior art; the invention provides a kind of synthetic method of 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters; greatly shorten synthetic route; in purge process, produce a small amount of active carbon residue; produce without other three wastes free from environmental pollution; and product yield is high, quality is good, is convenient to the advantages such as suitability for industrialized production.
Technical scheme: the synthetic method that the invention provides a kind of 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters, 2-methoxy-5-chlorobenzoic acid methyl esters, amino sulfinic acid sodium, solvent and catalyst are joined to reaction unit, control temperature 40～65 DEG C of reactions 8～16 hours; Reaction finishes, and adds activated carbon decolorizing, filters and removes active carbon, catalyst and byproduct sodium chloride; Filtrate obtains 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters through reduced pressure concentration.
Further, the synthetic method of above-mentioned 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters, described filtrate after reduced pressure concentration in 60 DEG C of vacuum drying.
Further, the synthetic method of above-mentioned 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters, described reaction unit is the reaction unit that reflux is housed.
Further, the synthetic method of above-mentioned 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters, described 2-methoxy-5-chlorobenzoic acid methyl esters, amino sulfinic acid sodium, solvent and catalyst are warming up to backflow in reaction unit, and being warming up to temperature is 40～65 DEG C.
Further, the synthetic method of above-mentioned 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters, described catalyst is stannous chloride.
Further, the synthetic method of above-mentioned 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters, the mol ratio of described 2-methoxy-5-chlorobenzoic acid methyl esters, amino sulfinic acid sodium and stannous chloride is 1:1.02～1.1:0.05～0.1.
Further, the synthetic method of above-mentioned 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters, is characterized in that: described solvent is oxolane.
Beneficial effect: compared with prior art; the present invention has the following advantages: the synthetic method of 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters of the present invention; advantage of the present invention is that former technological process is short; yield is high; quality is good; and the three wastes of nonpollution environment produce, very environmental protection, is applicable to large-scale industrial production.
Brief description of the drawings
Fig. 1 is the synthetic route chart of traditional handicraft 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters of the present invention;
Fig. 2 is the synthetic route chart of 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters of the present invention.
Detailed description of the invention
To, by several specific embodiments, further illustrate the present invention below, these embodiment, just in order to describe the problem, are not a kind of restriction.
Embodiment 1
Synthetic route as shown in Figure 2, in the 1000ml reaction bulb that reflux is housed, will add 300g oxolane, 50g(0.25mol) 2-methoxy-5-chlorobenzoic acid methyl esters, 1.25g stannous chloride (0.0125mol), 26.285g(0.255mol) amino sulfinic acid sodium, be warming up to 65 DEG C, and at this temperature, keep 12 hours, insulation finishes, in reactant liquor, add 2 grams of active carbons to take advantage of heat filtering, filtrate decompression is concentrated into dry, 60 DEG C of vacuum drying obtain, obtain 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters white crystals powder 57.9g(0.236mol), yield 94.5%, content 99.51%(HPLC).
Wherein HPLC testing conditions: mobile phase: 700 ml waters; 200 milliliters of methyl alcohol. Detect wavelength: 240nm, flow velocity 1.0ml/min, 0.01 gram, sample, is diluted to 25 milliliters, sample size 5 μ l with mobile phase.
Embodiment 2
Synthetic route as shown in Figure 2, in the 1000ml reaction bulb that reflux is housed, will add 300g oxolane, 50g(0.25mol) 2-methoxy-5-chlorobenzoic acid methyl esters, 2.5g(0.025mol) stannous chloride, 26.8g(0.26mol) amino sulfinic acid sodium, be warming up to 45 DEG C, and at this temperature, keep 16 hours, insulation finishes, in reactant liquor, add 2 grams of active carbons to take advantage of heat filtering, filtrate decompression is concentrated into dry, 60 DEG C of vacuum drying obtain, obtain 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters white crystals powder 58.3g(0.238mol), yield 95.09%, content 99.66%(HPLC).
Wherein HPLC testing conditions: mobile phase: 700 ml waters; 200 milliliters of methyl alcohol. Detect wavelength: 240nm, flow velocity 1.0ml/min, 0.01 gram, sample, is diluted to 25 milliliters, sample size 5 μ l with mobile phase.
Embodiment 3
Synthetic route as shown in Figure 2, in the 1000ml reaction bulb that reflux is housed, will add 300g oxolane, 50g(0.25mol) 2-methoxy-5-chlorobenzoic acid methyl esters, 2g(0.02mol) stannous chloride, 28.3g(0.275mol) amino sulfinic acid sodium, be warming up to 40 DEG C, and at this temperature, keep 8 hours, insulation finishes, in reactant liquor, add 2 grams of active carbons to take advantage of heat filtering, filtrate decompression is concentrated into dry, 60 DEG C of vacuum drying obtain, obtain 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters white crystals powder 59.2g(0.241mol), yield 96.55%, content 99.51%(HPLC).
Wherein HPLC testing conditions: mobile phase: 700 ml waters; 200 milliliters of methyl alcohol. Detect wavelength: 240nm, flow velocity 1.0ml/min, 0.01 gram, sample, is diluted to 25 milliliters, sample size 5 μ l with mobile phase.
From embodiment 1-3, advantage of the present invention is that former technological process is short, and yield is high, reaches more than 90%. And good product quality, traditional handicraft needs after purified can obtain content more than 99%, and what the present invention can be stable obtain content all reaches 99.5% above product.
The above is only several embodiments of invention, it should be pointed out that for those skilled in the art, not departing under the prerequisite of inventive principle, can also make some improvement, and these improve and also should be considered as protection scope of the present invention.
Claims (7)
1. a synthetic method for 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters, is characterized in that: 2-methoxy-5-chlorobenzoic acid methyl esters, amino sulfinic acid sodium, solvent and catalyst are joined to reaction unit, control temperature 40～65 DEG C of reactions 8～16 hours; Reaction finishes, and adds activated carbon decolorizing, filters and removes active carbon, catalyst and byproduct sodium chloride; Filtrate obtains 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters through reduced pressure concentration.
2. the synthetic method of 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters according to claim 1, is characterized in that: described filtrate after reduced pressure concentration in 60 DEG C of vacuum drying.
3. the synthetic method of 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters according to claim 1, is characterized in that: described reaction unit is the reaction unit that reflux is housed.
4. the synthetic method of 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters according to claim 3, is characterized in that: described 2-methoxy-5-chlorobenzoic acid methyl esters, amino sulfinic acid sodium, solvent and catalyst are warming up to 40～65 DEG C in reaction unit.
5. according to the synthetic method of the 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters described in claim 1 or 4, it is characterized in that: described catalyst is stannous chloride.
6. the synthetic method of 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters according to claim 5, is characterized in that: the mol ratio of described 2-methoxy-5-chlorobenzoic acid methyl esters, amino sulfinic acid sodium and stannous chloride is 1:1.02～1.1:0.05～0.1.
7. the synthetic method of 2-methoxyl group-5-sulfamoylbenzoic acid methyl esters according to claim 1, is characterized in that: described solvent is oxolane.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003055857A1 (en) * | 2001-12-28 | 2003-07-10 | Farmaceutsko-Hemijska Industrija 'zdravlje' | A process for synthesis of heterocyclic aminoalkyl benzamides |
| CN1884259A (en) * | 2006-06-08 | 2006-12-27 | 南开大学 | Process for preparing 2-methoxyl-5-amino sulfonyl methyl benzoate |
| CN103553990A (en) * | 2013-11-08 | 2014-02-05 | 苏州诚和医药化学有限公司 | Method for synthesizing 2-methoxyl-4-amino-5-ethylsulfonyl methyl benzoate by utilizing halogenation of halogen |
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- 2015-12-30 CN CN201511010527.3A patent/CN105601544A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003055857A1 (en) * | 2001-12-28 | 2003-07-10 | Farmaceutsko-Hemijska Industrija 'zdravlje' | A process for synthesis of heterocyclic aminoalkyl benzamides |
| CN1884259A (en) * | 2006-06-08 | 2006-12-27 | 南开大学 | Process for preparing 2-methoxyl-5-amino sulfonyl methyl benzoate |
| CN103553990A (en) * | 2013-11-08 | 2014-02-05 | 苏州诚和医药化学有限公司 | Method for synthesizing 2-methoxyl-4-amino-5-ethylsulfonyl methyl benzoate by utilizing halogenation of halogen |
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