CN103254106A - Preparation method of D-A type N,N-dimethylamino phenylthiourea - Google Patents
Preparation method of D-A type N,N-dimethylamino phenylthiourea Download PDFInfo
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- CN103254106A CN103254106A CN2012102496981A CN201210249698A CN103254106A CN 103254106 A CN103254106 A CN 103254106A CN 2012102496981 A CN2012102496981 A CN 2012102496981A CN 201210249698 A CN201210249698 A CN 201210249698A CN 103254106 A CN103254106 A CN 103254106A
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Abstract
The invention discloses a preparation method of D-A type N,N-dimethylamino phenylthiourea, which comprises the following steps: fetching carbon disulfide 4.3 ml, placing ammonia water 9.0 ml into a boiling flask with 3 necks, cooling wither ice and uniformly mixing; fetching substituted aniline 5.5 g and dissolving in 5 ml, slowly adding into the boiling flask with 3 necks drop by drop with continuously stirring, stirring, standing and obtaining the light yellow solid; adding distilled water 20 ml, slightly heating for completely dissolving the yellow solid, slowly stirring and adding a copper sulphate saturated solution 50 ml, uniformly stirring and standing; heating and refluxing the mixture, obtaining the yellow solution by a ethyl acetate extraction, dissolving substitute aniline 6.5g into 10 ml of ethanol, slowly stirring, adding the substitute aniline solution into the yellow solution, reacting, steaming the solvent and obtaining the products by recrystallization using 95% ethanol. The invention has the advantages of simple reaction technology, obvious iodide ion fluorescence identification effect, and is used as a momentarily prepared sensor with selectivity and sensitive signal mechanism.
Description
Technical field
The present invention relates to pharmaceutical preparation, that be specifically related to is D-A type N, the preparation method of N dimethylamino phenyl thiocarbamide.
Background technology
Design and synthetic to have the novel receptor that has the negatively charged ion measuring ability efficiently be one of environmental chemistry and biological important subject.In nervous activity and thyroid function, iodine plays an important role, and the shortage of iodine may cause the physiological function disorder, so the detection of iodine receives much concern.It is very important that the high responsive acceptor of development carries out the iodine detection.But because the iodine negatively charged ion has big ionic radius, characteristics such as electric density is low, and the hydrogen bond ability is low are so the iodide ion sensor is difficult to design.In addition, most incompatible with sensor and the water system of hydrogen bonded with iodide ion.The detection method of ultraviolet-visible light spectrum and fluorescence spectrum has highly sensitive, and the advantage of easy handling is widely used in anion monitoring; Yet, for the report of the fluorescence of iodide ion identification but seldom.In actual applications, can to prepare and have the sensor of selectivity and responsive signaling mechanism at any time be necessary in development.
Summary of the invention
For addressing the above problem, the invention provides D-A type N, the preparation method of N dimethylamino phenyl thiocarbamide is used for the fluorescence identification of iodide ion.
For realizing above-mentioned technical purpose, realize above-mentioned technique effect, the present invention is achieved through the following technical solutions:
D-A type N, the preparation method of N-dimethylamino phenyl thiocarbamide may further comprise the steps:
Step 1) is got dithiocarbonic anhydride 4.3ml, and ammoniacal liquor 9.0ml places there-necked flask, with the frozen water cooling, mixes; Get 5.5g substituted aniline 5ml dissolve with ethanol, under constantly stirring, slowly be added drop-wise in the there-necked flask, stir 1h, leave standstill 1h, obtain faint yellow solid;
Step 2) add 20ml distilled water, heating is dissolved described faint yellow solid fully slightly, stirs slowly to add 50ml copper sulfate saturated solution, stirs, and leaves standstill 2h;
Step 3) obtains yellow solution with the mixture heating up 1h that refluxes with ethyl acetate extraction, gets the 6.5g substituted aniline and is dissolved in the 10ml ethanol, stir down and slowly join in the described yellow solution, reacted 3 hours, and boiled off solvent, obtain target product with 95% ethyl alcohol recrystallization.
The reaction formula of step (1), (2), (3) synthesis technique is:
Further, described faint yellow solid is anilino dithio ammonium formiate.
The invention has the beneficial effects as follows:
Reaction process of the present invention is simple, and the fluorescence recognition effect of iodide ion is apparent in view, is a kind of sensor that can prepare and have selectivity and sensitive signal mechanism at any time.
Embodiment
Below in conjunction with embodiment, describe the present invention in detail.
D-A type N, the preparation method of N-dimethylamino phenyl thiocarbamide may further comprise the steps:
Step 1) is got dithiocarbonic anhydride 4.3ml, and ammoniacal liquor 9.0ml places there-necked flask, with the frozen water cooling, mixes; Get 5.5g substituted aniline 5ml dissolve with ethanol, under constantly stirring, slowly be added drop-wise in the there-necked flask, stir 1h, leave standstill 1h, obtain faint yellow solid;
Step 2) add 20ml distilled water, heating is dissolved described faint yellow solid fully slightly, stirs slowly to add 50ml copper sulfate saturated solution, stirs, and leaves standstill 2h;
Step 3) obtains yellow solution with the mixture heating up 1h that refluxes with ethyl acetate extraction, gets the 6.5g substituted aniline and is dissolved in the 10ml ethanol, stir down and slowly join in the described yellow solution, reacted 3 hours, and boiled off solvent, obtain target product with 95% ethyl alcohol recrystallization.
The reaction formula of step (1), (2), (3) synthesis technique is:
Further, described faint yellow solid is anilino dithio ammonium formiate.
Further, described D-A type N, 4-cyano group-4 '-N in the N-dimethylamino phenyl thiocarbamide, N-dimethylamino diphenyl thiourea and 4-ethanoyl-4 '-N, N-dimethylamino diphenyl thiourea are for the recognition principle of iodide ion:
2 * 10
-5MolL
-14-cyano group-4 '-N; N-dimethylamino diphenyl thiourea and 4-ethanoyl-4 '-N; N-dimethylamino diphenyl thiourea THF solution in add the Halothane iodide ion of 5 times of thiourea concentrations respectively; wherein iodide ion makes 4-cyano group-4 '-N; N-dimethylamino diphenyl thiourea and 4-ethanoyl-4 '-N, the charge transfer fluorescence at 480nm and 520nm of N-dimethylamino diphenyl thiourea is buried in oblivion.
Claims (2)
1. D-A type N, the preparation method of N-dimethylamino phenyl thiocarbamide is characterized in that, may further comprise the steps:
Step 1) is got dithiocarbonic anhydride 4.3ml, and ammoniacal liquor 9.0ml places there-necked flask, with the frozen water cooling, mixes; Get 5.5g substituted aniline 5ml dissolve with ethanol, under constantly stirring, slowly be added drop-wise in the there-necked flask, stir 1h, leave standstill 1h, obtain faint yellow solid;
Step 2) add 20ml distilled water, heating is dissolved described faint yellow solid fully slightly, stirs slowly to add 50ml copper sulfate saturated solution, stirs, and leaves standstill 2h;
Step 3) obtains yellow solution with the mixture heating up 1h that refluxes with ethyl acetate extraction, gets the 6.5g substituted aniline and is dissolved in the 10ml ethanol, slowly join in the described yellow solution under stirring, reacted 3 hours, boil off solvent, obtain target product with 95% ethyl alcohol recrystallization
The reaction formula of step (1), (2), (3) synthesis technique is:
2. D-A type N according to claim 1, the preparation method of N-dimethylamino phenyl thiocarbamide is characterized in that: described faint yellow solid is anilino dithio ammonium formiate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012102496981A CN103254106A (en) | 2012-07-19 | 2012-07-19 | Preparation method of D-A type N,N-dimethylamino phenylthiourea |
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| CN2012102496981A CN103254106A (en) | 2012-07-19 | 2012-07-19 | Preparation method of D-A type N,N-dimethylamino phenylthiourea |
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| CN103254106A true CN103254106A (en) | 2013-08-21 |
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| CN2012102496981A Pending CN103254106A (en) | 2012-07-19 | 2012-07-19 | Preparation method of D-A type N,N-dimethylamino phenylthiourea |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610117A (en) * | 2015-02-21 | 2015-05-13 | 桂林理工大学 | Bis-phenylthiourea and application thereof |
| CN104610116A (en) * | 2015-02-21 | 2015-05-13 | 桂林理工大学 | Bis-phenyl thiourea derivative and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636104A (en) * | 1968-10-29 | 1972-01-18 | Olin Mathieson | Process for preparing n n'-diarylthioureas |
-
2012
- 2012-07-19 CN CN2012102496981A patent/CN103254106A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636104A (en) * | 1968-10-29 | 1972-01-18 | Olin Mathieson | Process for preparing n n'-diarylthioureas |
Non-Patent Citations (3)
| Title |
|---|
| 吴芳英，等: "硫脲类阴离子受体的设计合成与阴离子识别", 《分析试验室》 * |
| 沈铁焕，等: "N,N"-二苯基硫脲的研制", 《河北化工》 * |
| 陈国广，等: "对称和非对称取代硫脲的合成", 《精细化工》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610117A (en) * | 2015-02-21 | 2015-05-13 | 桂林理工大学 | Bis-phenylthiourea and application thereof |
| CN104610116A (en) * | 2015-02-21 | 2015-05-13 | 桂林理工大学 | Bis-phenyl thiourea derivative and application thereof |
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Application publication date: 20130821 |