CN101230027B - Method for preparing S-para methylbenzyl cysteine hydrochloride - Google Patents
Method for preparing S-para methylbenzyl cysteine hydrochloride Download PDFInfo
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- CN101230027B CN101230027B CN2008100431420A CN200810043142A CN101230027B CN 101230027 B CN101230027 B CN 101230027B CN 2008100431420 A CN2008100431420 A CN 2008100431420A CN 200810043142 A CN200810043142 A CN 200810043142A CN 101230027 B CN101230027 B CN 101230027B
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- cysteine hydrochloride
- methylbenzyl
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Abstract
The invention relates to a method for preparing a S-p-methylbenzyl cysteine hydrochloride, and mainly aims at solving the technical problems of prior art that (1) the use of trifluoroacetate results in high cost and strong corrosiveness and (2) water is used as reaction medium owing to the use of organic solvents. The invention has the technical proposal that: a method for the preparation of S-p-methylbenzyl cysteine hydrochloride is characterized in that the S- p-methylbenzyl cysteine hydrochloride is directly generated by using the dilute hydrochloric acid as the reaction medium and making the cysteine hydrochloride directly react with the methyl-benzenemethanol. The invention provides a method for producing the S-p-methylbenzyl cysteine hydrochloride in large scale.
Description
Technical field: the present invention relates to the preparation method of a kind of S-to methylbenzyl cysteine hydrochloride.
Background technology: existing preparation S-is generally the method for methylbenzyl cysteine hydrochloride: make solvent with methylene dichloride, with cysteine hydrochloride and to methylbenzyl alcohol (or to methyl benzyl chloride or p-tolyl aldehyde) in the presence of trifluoroacetic acid, reaction generates S-to methylbenzyl cysteine hydrochloride (Tetrahedron.Lett, 1994,1631-1634), this kind method is because of using trifluoroacetic acid, and cost is higher, and corrodibility is strong, and is dangerous high.
Summary of the invention: the purpose of this invention is to provide the preparation method of a kind of S-to methylbenzyl cysteine hydrochloride, solve mainly that existing preparation method exists because of using trifluoroacetic acid to cause cost higher, and the strong technical problem of corrodibility and avoid using the technical problem of organic solvents such as methylene dichloride.
Technical scheme of the present invention is: a kind of S-is to the preparation method of methylbenzyl cysteine hydrochloride, it is characterized in that: use dilute hydrochloric acid as reaction medium, generate S-to methylbenzyl cysteine hydrochloride with cysteine hydrochloride with to the methylbenzyl alcohol direct reaction.
The invention has the beneficial effects as follows: synthetic simple, avoid with an organic solvent and trifluoroacetic acid, help environmental protection, and cost is low, the productive rate height is convenient to large-scale production.
Embodiment:
A kind of S-uses dilute hydrochloric acid as reaction medium to the preparation method of methylbenzyl cysteine hydrochloride, generates S-to methylbenzyl cysteine hydrochloride with cysteine hydrochloride with to the methylbenzyl alcohol direct reaction.The hydrochloric acid consumption is 0.1～2 equivalent, and reaction need be carried out reflux 2～24 hours, and preferred reaction need be carried out reflux 3～12 hours.
Embodiment one:
1,1.33 kilograms cysteine hydrochloride is dissolved in 9 liter of 0.2 normal hydrochloric acid, stirs;
2, add 1 kilogram to methylbenzyl alcohol;
3, reflux is 12 hours;
4, stop heating, reaction solution is added in 40 premium on currency, cooling promptly has solid to separate out;
5, filter, oven dry gets 1.65 kilograms of S-to methylbenzyl cysteine hydrochloride.
Embodiment two:
1,1.33 kilograms cysteine hydrochloride is dissolved in 9 liter of 0.4 normal hydrochloric acid, stirs;
2, add 1 kilogram to methylbenzyl alcohol;
3, reflux is 11 hours;
4, stop heating, reaction solution is added in 40 premium on currency, cooling promptly has solid to separate out;
5, filter, oven dry gets 1.65 kilograms of S-to methylbenzyl cysteine hydrochloride.
Embodiment three:
1,1.33 kilograms cysteine hydrochloride is dissolved in 9 liter of 0.6 normal hydrochloric acid, stirs;
2, add 1 kilogram to methylbenzyl alcohol;
3, reflux is 10 hours;
4, stop heating, reaction solution is added in 40 premium on currency, cooling promptly has solid to separate out;
5, filter, oven dry gets 1.65 kilograms of S-to methylbenzyl cysteine hydrochloride.
Embodiment four:
1,1.33 kilograms cysteine hydrochloride is dissolved in 9 liter of 0.8 normal hydrochloric acid, stirs;
2, add 1 kilogram to methylbenzyl alcohol;
3, reflux is 9 hours;
4, stop heating, reaction solution is added in 40 premium on currency, cooling promptly has solid to separate out;
5, filter, oven dry gets 1.65 kilograms of S-to methylbenzyl cysteine hydrochloride.
Embodiment five:
1,1.33 kilograms cysteine hydrochloride is dissolved in 9 liter of 1 normal hydrochloric acid, stirs;
2, add 1 kilogram to methylbenzyl alcohol;
3, reflux is 8 hours;
4, stop heating, reaction solution is added in 40 premium on currency, cooling promptly has solid to separate out;
5, filter, oven dry gets 1.65 kilograms of S-to methylbenzyl cysteine hydrochloride.
Embodiment six:
1,1.33 kilograms cysteine hydrochloride is dissolved in 9 liter of 1.2 normal hydrochloric acid, stirs;
2, add 1 kilogram to methylbenzyl alcohol;
3, reflux is 7 hours;
4, stop heating, reaction solution is added in 40 premium on currency, cooling promptly has solid to separate out;
5, filter, oven dry gets 1.65 kilograms of S-to methylbenzyl cysteine hydrochloride.
Embodiment seven:
1,1.33 kilograms cysteine hydrochloride is dissolved in 9 liter of 1.4 normal hydrochloric acid, stirs;
2, add 1 kilogram to methylbenzyl alcohol;
3, reflux is 6 hours;
4, stop heating, reaction solution is added in 40 premium on currency, cooling promptly has solid to separate out;
5, filter, oven dry gets 1.65 kilograms of S-to methylbenzyl cysteine hydrochloride.
Embodiment eight:
1,1.33 kilograms cysteine hydrochloride is dissolved in 9 liter of 1.6 normal hydrochloric acid, stirs;
2, add 1 kilogram to methylbenzyl alcohol;
3, reflux is 5 hours;
4, stop heating, reaction solution is added in 40 premium on currency, cooling promptly has solid to separate out;
5, filter, oven dry gets 1.65 kilograms of S-to methylbenzyl cysteine hydrochloride.
Embodiment nine:
1,1.33 kilograms cysteine hydrochloride is dissolved in 9 liter of 2 normal hydrochloric acid, stirs;
2, add 1 kilogram to methylbenzyl alcohol;
3, reflux is 3 hours;
4, stop heating, reaction solution is added in 40 premium on currency, cooling promptly has solid to separate out;
5, filter, oven dry gets 1.65 kilograms of S-to methylbenzyl cysteine hydrochloride.
Claims (3)
1. a S-is to the preparation method of methylbenzyl cysteine hydrochloride, it is characterized in that using 0.1～2 equivalent dilute hydrochloric acid as reaction medium, generate S-to methylbenzyl cysteine hydrochloride with cysteine hydrochloride with to the methylbenzyl alcohol direct reaction, reaction need be carried out reflux 2～24 hours.
2. according to the preparation method of the described a kind of S-of claim 1, it is characterized in that reacting and to carry out reflux 3～12 hours methylbenzyl cysteine hydrochloride.
3. a kind of S-according to claim 1 is characterized in that to the preparation method of methylbenzyl cysteine hydrochloride the reaction solution after the reflux need cool off.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008100431420A CN101230027B (en) | 2008-02-22 | 2008-02-22 | Method for preparing S-para methylbenzyl cysteine hydrochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008100431420A CN101230027B (en) | 2008-02-22 | 2008-02-22 | Method for preparing S-para methylbenzyl cysteine hydrochloride |
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| Publication Number | Publication Date |
|---|---|
| CN101230027A CN101230027A (en) | 2008-07-30 |
| CN101230027B true CN101230027B (en) | 2011-03-23 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2008100431420A Active CN101230027B (en) | 2008-02-22 | 2008-02-22 | Method for preparing S-para methylbenzyl cysteine hydrochloride |
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| CN (1) | CN101230027B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0023578A1 (en) * | 1979-07-03 | 1981-02-11 | Shionogi & Co., Ltd. | Aminoalkylbenzene derivatives, process for their preparation and pharmaceutical compositions |
| CN1919847A (en) * | 2006-09-21 | 2007-02-28 | 中国人民解放军第二军医大学 | Novel hydrochloride compound and use thereof |
-
2008
- 2008-02-22 CN CN2008100431420A patent/CN101230027B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0023578A1 (en) * | 1979-07-03 | 1981-02-11 | Shionogi & Co., Ltd. | Aminoalkylbenzene derivatives, process for their preparation and pharmaceutical compositions |
| CN1919847A (en) * | 2006-09-21 | 2007-02-28 | 中国人民解放军第二军医大学 | Novel hydrochloride compound and use thereof |
Non-Patent Citations (8)
| Title |
|---|
| Lutz S. Richter, et al..Two New Procedures for the Introduction of Benzyl-typeProtecting Groups for Thiols.Tetrahedron Lett.35 11.1994,35(11),1631-1634. |
| Lutz S. Richter, et al..Two New Procedures for the Introduction of Benzyl-typeProtecting Groups for Thiols.Tetrahedron Lett.35 11.1994,35(11),1631-1634. * |
| 姚斌，等.新型中枢兴奋药物***的合成新工艺.第二军医大学学报22 3.2001,22(3),293-294. |
| 姚斌等.新型中枢兴奋药物***的合成新工艺.第二军医大学学报22 3.2001,22(3),293-294. * |
| 窦清玉，等.***的合成.中国医药工业杂志33 3.2002,33(3),110-111. |
| 窦清玉等.***的合成.中国医药工业杂志33 3.2002,33(3),110-111. * |
| 陈梅筠.新型中枢兴奋药物***的合成.化工时刊18 4.2004,18(4),33-34. |
| 陈梅筠.新型中枢兴奋药物***的合成.化工时刊18 4.2004,18(4),33-34. * |
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| CN101230027A (en) | 2008-07-30 |
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