CN104650158A - Method for synthesizing acetylferrocene hydrazone - Google Patents
Method for synthesizing acetylferrocene hydrazone Download PDFInfo
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- CN104650158A CN104650158A CN201510071742.8A CN201510071742A CN104650158A CN 104650158 A CN104650158 A CN 104650158A CN 201510071742 A CN201510071742 A CN 201510071742A CN 104650158 A CN104650158 A CN 104650158A
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- hydrazone
- reaction
- ferrocene
- synthesis
- methyl ketone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
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Abstract
The invention discloses a method for synthesizing acetylferrocene hydrazone. The method comprises the following steps: uniformly stirring and mixing acetic anhydride and phosphoric acid, adding ferrocene so that ferrocene is subjected to an acetyl reaction; washing, performing suction filtration and drying after the reaction is complete, thereby obtaining acetylferrocene solids; adding the acetylferrocene into absolute ethyl alcohol, uniformly stirring, adding hydrazine hydrate, and detecting the reaction progress by using thin-layer chromatography; and purifying and separating the acetylferrocene hydrazone by using column-layer chromatography after the reaction is completed. According to the method, the reaction conditions are mild, the temperature is easy to control, and the preparation yield is high.
Description
Technical field
The present invention relates to organic synthesis field, be specifically related to a kind of method of synthesis of acetyl base ferrocene hydrazone.
Background technology
Ferrocene (C
10h
10fe) have another name called Dicyclopentadiene (DCPD) and close iron, cyclopentadiene iron, its special sandwich structure makes it present special chemical property, namely two luxuriant rings can be introduced the substituting group containing various functional group, as aldehyde, ketone, acid and acyl chlorides, amine, alcohol, halogen, metal etc.Ferrocene and its derivative chemical structure is special, and its group has the features such as aromaticity, oxidation-reduction quality, stability and hypotoxicity, makes it have a wide range of applications in many fields such as electrochemistry and Photochemical Function material, medicine, analyses
Ferrocene is introduced the active structure of hydrazone compounds, utilize the special chemical of ferrocene, physical properties, the object of the activity improving hydrazone heterocyclic compounds can be reached; Simultaneously their combination has in bioactive molecular aggregates to same a part two kinds and realizes its active superposition, for explore and the novel derivative tool synthesizing a class high biological activity is of great significance.
Summary of the invention
The object of the present invention is to provide a kind of method of synthesis of acetyl base ferrocene hydrazone, this reaction conditions gentleness, temperature are easy to control, and prepare productive rate higher.
For achieving the above object, technical scheme provided by the invention is:
A method for synthesis of acetyl base ferrocene hydrazone, comprising:
Step 1: add diacetyl oxide and phosphoric acid in there-necked flask, add ferrocene after stirring; Be warming up to 50-70 DEG C, the reaction times is 1-2h;
Step 2: reaction solution is poured into and is equipped with in the beaker of trash ice, add NaHCO
3neutralization; Suction filtration, collect and separate out solid, it is brown for being washed to solid, and product room temperature is placed dry;
Step 3: spherical condensation tube is being housed, adds dehydrated alcohol and ferrocenyl methyl ketone, adds hydrazine hydrate after stirring, ferrocenyl methyl ketone in the there-necked flask of glass stopper and stirring rod: hydrazine hydrate mass ratio=57: 25-50; Cold-water reflux also stirs, and with heating in water bath to 40-80 DEG C, the reaction times is 3-5h;
Step 4: poured into by reaction solution in round-bottomed flask, uses the ethanol in vacuum distillation apparatus removal reaction solution instead, uses column chromatography purification & isolation ferrocenyl methyl ketone hydrazone afterwards again.
Preferably, the method for described a kind of synthesis of acetyl base ferrocene hydrazone, it is characterized in that, described step 1 test temperature is 50 DEG C, and the reaction times is 1 hour.
Preferably, the method for described a kind of synthesis of acetyl base ferrocene hydrazone, is characterized in that, uses phosphoric acid in NaHCO3 and unnecessary in described step 2.
Preferably, the method for described a kind of synthesis of acetyl base ferrocene hydrazone, is characterized in that, diacetyl oxide in described step 1: phosphoric acid: ferrocene mass ratio is 51: 490: 279.
Preferably, the method for described a kind of synthesis of acetyl base ferrocene hydrazone, is characterized in that, ferrocenyl methyl ketone in described step 3: hydrazine hydrate mass ratio=57: 25-50.
Preferably, the method for a kind of synthesis of acetyl base ferrocene hydrazone described in 1, it is characterized in that, in described step 3, optimal reaction temperature is 60-80 DEG C, and the reaction times is 3 hours.
Preferably, the method for described a kind of synthesis of acetyl base ferrocene hydrazone, it is characterized in that, described step 1,3 monitors extent of reaction with thin layer chromatography.
Beneficial effect of the present invention is that synthetic reaction condition is gentle, temperature is easy to control, and prepares productive rate high.
Accompanying drawing explanation
Fig. 1 is the reaction equation of step 1 of the present invention.
Fig. 2 is the reaction equation of step 3 of the present invention.
Embodiment
Below in conjunction with in conjunction with the present invention preferably specific embodiment the present invention is described in further details.As
Embodiment 1
The first step: in 250mL there-necked flask, adds 10.200g (0.1mol) diacetyl oxide and 3.460g (0.03mol) 85% phosphoric acid, and stir 15min, both add ferrocene 3.720g (0.01mol) after mixing.Be warming up to 50 DEG C, system is orange, reacts 1h at this temperature, with thin-layer chromatography monitoring reaction, when the faint yellow colour band of ferrocene on thin layer plate disappears, illustrates that reaction has been carried out completely, now stopped reaction.Reaction mixture is poured in the beaker that 20g trash ice is housed, adds NaHCO
3neutralize unnecessary phosphoric acid, stir till bubble-free produces.Suction filtration also collects precipitation solid, and it is brown for being washed to solid, and product room temperature is placed dry, and weigh to obtain ferrocenyl methyl ketone brown-red solid 2.56g, and this step productive rate reaches 89%.
Second step: spherical condensation tube is being housed; the ferrocenyl methyl ketone of 20mL dehydrated alcohol and 1.140g (0.005mol) is added in the 250mL there-necked flask of glass stopper and stirring rod; stir 15min; add the hydrazine hydrate of 1.012g (0.02mol); cold-water reflux; stir, heating in water bath to 60 DEG C.Just start to use thin-layer chromatography detection reaction in reflection, reacted after three hours and stop.Reaction solution is poured in 50mL round-bottomed flask, use the ethanol in vacuum distillation apparatus removal reaction solution instead, use the rose solid 0.666g of column chromatography purification & isolation ferrocenyl methyl ketone hydrazone afterwards again, productive rate 55%.
Embodiment 2
The first step: in 250mL there-necked flask, adds 10.200g (0.1mol) diacetyl oxide and 3.460g (0.03mol) 85% phosphoric acid, and stir 15min, both add ferrocene 3.720g (0.01mol) after mixing.Be warming up to 50 DEG C, system is orange, reacts 1h at this temperature, with thin-layer chromatography monitoring reaction, when the faint yellow colour band of ferrocene on thin layer plate disappears, illustrates that reaction has been carried out completely, now stopped reaction.Reaction mixture is poured in the beaker that 20g trash ice is housed, adds NaHCO
3neutralize unnecessary phosphoric acid, stir till bubble-free produces.Suction filtration also collects precipitation solid, and it is brown for being washed to solid, and product room temperature is placed dry, and weigh to obtain ferrocenyl methyl ketone brown-red solid 2.56g, and this step productive rate reaches 89%.
Second step: spherical condensation tube is being housed; the ferrocenyl methyl ketone of 20mL dehydrated alcohol and 1.14g (0.005mol) is added in the 250mL there-necked flask of glass stopper and stirring rod; fully mix both when being stirred to 15min; add the hydrazine hydrate of 1.012g (0.02mol); cold-water reflux; stir, heating in water bath to 70 DEG C.Just start to use thin-layer chromatography detection reaction in reflection, reacted after three hours and stop.Reaction solution is poured in 50mL round-bottomed flask, use the ethanol in vacuum distillation apparatus removal reaction solution instead, use the rose solid 0.750g of column chromatography purification & isolation ferrocenyl methyl ketone hydrazone afterwards again, productive rate 62%.
Embodiment 3
The first step: in 250mL there-necked flask, adds 10.200g (0.1mol) diacetyl oxide and 3.460g (0.03mol) 85% phosphoric acid, and stir 15min, both add ferrocene 3.720g (0.01mol) after mixing.Be warming up to 50 DEG C, system is orange, reacts 1h at this temperature, with thin-layer chromatography monitoring reaction, when the faint yellow colour band of ferrocene on thin layer plate disappears, illustrates that reaction has been carried out completely, now stopped reaction.Reaction mixture is poured in the beaker that 20g trash ice is housed, adds NaHCO
3neutralize unnecessary phosphoric acid, stir till bubble-free produces.Suction filtration also collects precipitation solid, and it is brown for being washed to solid, and product room temperature is placed dry, and weigh to obtain ferrocenyl methyl ketone brown-red solid 2.56g, and this step productive rate reaches 89%.
Second step: spherical condensation tube is being housed; the ferrocenyl methyl ketone of 20mL dehydrated alcohol and 1.14g (0.005mol) is added in the 250mL there-necked flask of glass stopper and stirring rod; fully mix both when being stirred to 15min; add the hydrazine hydrate of 1.012g (0.02mol); cold-water reflux; stir, heating in water bath to 70 DEG C.Just start to use thin-layer chromatography detection reaction in reflection, reacted after three hours and stop.Reaction solution is poured in 50mL round-bottomed flask, use the ethanol in vacuum distillation apparatus removal reaction solution instead, use the rose solid 0.702g of column chromatography purification & isolation ferrocenyl methyl ketone hydrazone afterwards again, productive rate 58%.
Embodiment 4
The first step: in 250mL there-necked flask, adds 10.200g (0.1mol) diacetyl oxide and 3.460g (0.03mol) 85% phosphoric acid, and stir 15min, both add ferrocene 3.720g (0.01mol) after mixing.Be warming up to 50 DEG C, system is orange, reacts 1h at this temperature, with thin-layer chromatography monitoring reaction, when the faint yellow colour band of ferrocene on thin layer plate disappears, illustrates that reaction has been carried out completely, now stopped reaction.Reaction mixture is poured in the beaker that 20g trash ice is housed, adds NaHCO
3neutralize unnecessary phosphoric acid, stir till bubble-free produces.Suction filtration also collects precipitation solid, and it is brown for being washed to solid, and product room temperature is placed dry, and weigh to obtain ferrocenyl methyl ketone brown-red solid 2.56g, and this step productive rate reaches 89%.
Second step: spherical condensation tube is being housed; the ferrocenyl methyl ketone of 20mL dehydrated alcohol and 1.14g (0.005mol) is added in the 250mL there-necked flask of glass stopper and stirring rod; fully mix both when being stirred to 15min; add the hydrazine hydrate of 0.759g (0.015mol); cold-water reflux; stir, heating in water bath to 70 DEG C.Just start to use thin-layer chromatography detection reaction in reflection, reacted after three hours and stop.Reaction solution is poured in 50mL round-bottomed flask, use the ethanol in vacuum distillation apparatus removal reaction solution instead, use the rose solid 0.605g of column chromatography purification & isolation ferrocenyl methyl ketone hydrazone afterwards again, productive rate 50%.
Embodiment 5
The first step: in 250mL there-necked flask, adds 10.200g (0.1mol) diacetyl oxide and 3.460g (0.03mol) 85% phosphoric acid, and stir 15min, both add ferrocene 3.720g (0.01mol) after mixing.Be warming up to 50 DEG C, system is orange, reacts 1h at this temperature, with thin-layer chromatography monitoring reaction, when the faint yellow colour band of ferrocene on thin layer plate disappears, illustrates that reaction has been carried out completely, now stopped reaction.Reaction mixture is poured in the beaker that 20g trash ice is housed, adds NaHCO
3neutralize unnecessary phosphoric acid, stir till bubble-free produces.Suction filtration also collects precipitation solid, and it is brown for being washed to solid, and product room temperature is placed dry, and weigh to obtain ferrocenyl methyl ketone brown-red solid 2.56g, and this step productive rate reaches 89%.
Second step: spherical condensation tube is being housed; the ferrocenyl methyl ketone of 20mL dehydrated alcohol and 1.14g (0.005mol) is added in the 250mL there-necked flask of glass stopper and stirring rod; fully mix both when being stirred to 15min; add the hydrazine hydrate of 0.500g (0.01mol); cold-water reflux; stir, heating in water bath to 70 DEG C.Just start to use thin-layer chromatography detection reaction in reflection, reacted after three hours and stop.Reaction solution is poured in 50mL round-bottomed flask, use the ethanol in vacuum distillation apparatus removal reaction solution instead, use the rose solid 0.508g of column chromatography purification & isolation ferrocenyl methyl ketone hydrazone afterwards again, productive rate 42%.
Comparing embodiment 1-3, when other reaction conditionss are identical, temperature of reaction be 60 DEG C, 70 DEG C and 80 DEG C time, the productive rate of product ferrocenyl methyl ketone hydrazone is respectively 55%, 62% and 58%, illustrate 70 DEG C for reaction optimum temps; When 60 DEG C, thin-layer chromatography detects and still has ferrocenyl methyl ketone not react, and illustrates that reaction is carried out not exclusively; When 80 DEG C, thin-layer chromatography detects that by product two-(ferrocenyl methyl ketone) dihydrazone generates, and illustrates that the too high by product that is easy to of temperature generates.
Comparing embodiment 3-5, when other reaction conditionss are identical, when ferrocenyl methyl ketone and hydrazine hydrate mol ratio are 1: 4,1: 3,1: 2, the productive rate of product ferrocenyl methyl ketone hydrazone is respectively 62%, 50%, 42%, illustrates 1: 4 to be the optimum mole ratio of ferrocenyl methyl ketone and hydrazine hydrate; When mol ratio is 1: 2 and 1: 3, thin-layer chromatography all detects that by product two-(ferrocenyl methyl ketone) dihydrazone generates.This embodiment comparative descriptions improves the generation that hydrazine hydrate consumption is conducive to suppressing by product.
Product ferrocenyl methyl ketone hydrazone does infrared measurement has absorption peak near 3408cm-1 and 3391cm-1, shows that product has-NH: exist, have several absorption peak near 3089.40cm-1, and explanation is that 8C-H exists; Occurred the absorption peak of three medium tenacitys at 810cm-1,997cm-1 and 1102cm-1 place, the stretching vibration of the skeleton C=C double bond respectively on the 8C-H out-of-plane deformation vibration of luxuriant ring, in-plane bending vibration and luxuriant ring is inhaled near 1638cm-1 and is had absorption peak to show there is C=N key.
Although embodiment of the present invention are open as above, but it is not restricted to listed in specification sheets and embodiment utilization, it can be applied to various applicable the field of the invention completely, for those skilled in the art, can easily realize other amendment, therefore do not deviating under the universal that claim and equivalency range limit, the present invention is not limited to specific details and illustrates here and the legend described.
Claims (7)
1. a method for synthesis of acetyl base ferrocene hydrazone, is characterized in that, comprise the following steps:
Step 1: add diacetyl oxide and phosphoric acid in there-necked flask, add ferrocene after stirring; Be warming up to 50-70 DEG C, the reaction times is 1-2h;
Step 2: reaction solution is poured into and is equipped with in the beaker of trash ice, add NaHCO
3neutralization; Suction filtration, collect and separate out solid, it is brown for being washed to solid, and product room temperature is placed dry;
Step 3: spherical condensation tube is being housed, adds dehydrated alcohol and ferrocenyl methyl ketone, adds hydrazine hydrate after stirring, ferrocenyl methyl ketone in the there-necked flask of glass stopper and stirring rod: hydrazine hydrate mass ratio=57: 25-50; Cold-water reflux also stirs, and with heating in water bath to 40-80 DEG C, the reaction times is 3-5h;
Step 4: poured into by reaction solution in round-bottomed flask, uses the ethanol in vacuum distillation apparatus removal reaction solution instead, uses column chromatography purification & isolation ferrocenyl methyl ketone hydrazone afterwards again.
2. the method for a kind of synthesis of acetyl base ferrocene hydrazone as claimed in claim 1, it is characterized in that, described step 1 test temperature is 50 DEG C, and the reaction times is 1 hour.
3. the method for a kind of synthesis of acetyl base ferrocene hydrazone as claimed in claim 1, is characterized in that, use NaHCO in described step 2
3neutralize unnecessary phosphoric acid.
4. the method for a kind of synthesis of acetyl base ferrocene hydrazone as claimed in claim 1 or 2, is characterized in that, diacetyl oxide in described step 1: phosphoric acid: ferrocene mass ratio is 51: 490: 279.
5. the method for a kind of synthesis of acetyl base ferrocene hydrazone as claimed in claim 1, is characterized in that, ferrocenyl methyl ketone in described step 3: hydrazine hydrate mass ratio=57: 25-50.
6. the method for a kind of synthesis of acetyl base ferrocene hydrazone as claimed in claim 1, it is characterized in that, in described step 3, optimal reaction temperature is 60-80 DEG C, and the reaction times is 3 hours.
7. the method for a kind of synthesis of acetyl base ferrocene hydrazone as claimed in claim 1, it is characterized in that, described step 1,3 monitors extent of reaction with thin layer chromatography.
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| CN201510071742.8A CN104650158A (en) | 2015-02-11 | 2015-02-11 | Method for synthesizing acetylferrocene hydrazone |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107383112A (en) * | 2017-07-24 | 2017-11-24 | 郑州轻工业学院 | The synthetic method of ferrocenyl miazines multidentate ligand and its application in Heck reactions |
| CN107488199A (en) * | 2016-06-13 | 2017-12-19 | 苏州天允金属材料有限公司 | The synthetic method of α bromoacetylferrocenes |
| CN107488200A (en) * | 2016-06-13 | 2017-12-19 | 苏州天允金属材料有限公司 | A kind of synthetic method of ferrocenyl methyl ketone |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102276659A (en) * | 2011-06-29 | 2011-12-14 | 上海大学 | Monoacyl ferrocene Schiff base amido cyclotriphosphazene and synthetic method thereof |
-
2015
- 2015-02-11 CN CN201510071742.8A patent/CN104650158A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276659A (en) * | 2011-06-29 | 2011-12-14 | 上海大学 | Monoacyl ferrocene Schiff base amido cyclotriphosphazene and synthetic method thereof |
Non-Patent Citations (3)
| Title |
|---|
| A.G. OSBORNE等,: "Synthetic, structural and electrochemical studies on some ferrocenylazines: crystal structures of [4](1)(1,4-dimethyl-2,3-diazabuta-1,3-dien)ferrocenophane and [42](1,1’)bis(1,4-dimethyl-2,3-diazabuta-1,3-dien)ferrocenophane", 《JOURNAL OF ORGANOMETALLIC CHEMISTRY》 * |
| BENNO BILDSTEIN等,: "N-Dimethylaluminum-N’,N’-dimethylhydrazide: a new and efficient reagent for the synthesis of N,N-dimethylhydrazones and N-unsubstituted hydrazones", 《SYNTHESIS》 * |
| ZHANG SHU-SHENG等,: "Facile Synthesis and Characterization of Bioactive N-[(1-Ferrocenylethylidene)amino]-N’-β-D-glycopyranosylthiourea", 《CHINESE JOURNAL OF CHEMISTRY》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107488199A (en) * | 2016-06-13 | 2017-12-19 | 苏州天允金属材料有限公司 | The synthetic method of α bromoacetylferrocenes |
| CN107488200A (en) * | 2016-06-13 | 2017-12-19 | 苏州天允金属材料有限公司 | A kind of synthetic method of ferrocenyl methyl ketone |
| CN107383112A (en) * | 2017-07-24 | 2017-11-24 | 郑州轻工业学院 | The synthetic method of ferrocenyl miazines multidentate ligand and its application in Heck reactions |
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Application publication date: 20150527 |