CN104558057A - Method for preparing carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole - Google Patents

Method for preparing carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole Download PDF

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CN104558057A
CN104558057A CN201510026286.5A CN201510026286A CN104558057A CN 104558057 A CN104558057 A CN 104558057A CN 201510026286 A CN201510026286 A CN 201510026286A CN 104558057 A CN104558057 A CN 104558057A
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amino
thiadiazoles
ferrocene
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crude product
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刘玉婷
杨阿宁
尹大伟
吕博
黄涛
吴倩倩
王雨薇
许娟娟
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Shaanxi University of Science and Technology
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    • 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 preparing carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole. The method comprises the following steps: adding A mol of carbonyl ferrocene, B mol of 2-amino-5-substituted-1,3,4-thiadiazole and C mol of p-toluenesulfonic acid into a dried mortar, grinding at room temperature until the raw material reaction (a TLC monitoring reaction) is complete, preserving the temperature in a drying box under the condition of 50 DEG C for 30 minutes, cooling to room temperature, adding absolute ethyl alcohol, performing suction filtration on the mixed solution, removing the catalyst p-toluenesulfonic acid, performing vacuum concentration until the filtrate is dried, thereby obtaining the crude product, wherein the ratio of A to B to C is 1:(1.0-1.2):(1.0-1.2); and recrystallizing the crude product by using absolute ethyl alcohol, thereby obtaining the purified product. The method disclosed by the invention is short in reaction time, mild in reaction conditions, low in equipment requirements, easy to operate and simple in after-treatment and is a green, economic, environment-friendly and high-efficiency method for synthesizing the carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole, a solvent is not needed, the catalyst can be repeatedly used, and the yield is over 85 percent.

Description

One prepares the method that acyl Ferrocene contracting 2-amino-5-replaces-1,3,4-thiadiazoles
Technical field
The invention belongs to the field of chemical synthesis, particularly one prepares the method that acyl Ferrocene contracting 2-amino-5-replaces-1,3,4-thiadiazoles.
Background technology
1,3,4-thiadiazole compound is a kind of containing the heteroatomic important heterogeneous ring compound of N, C, S, with aromatic nucleus comparing class seemingly, there is aromaticity and conjugative effect.Its substituted aryl can as active group and multiple compounds generation chemical reaction, and therefore substituting group is that the thiadiazole compound of active group is often by as organic synthesis active intermediate.Have anticancer, AntiHIV1 RT activity, antiviral and antimycotic in medical, in agricultural chemicals, have the effects such as desinsection, antibacterial, weeding, plant growth regulating, acyl Ferrocene has sandwich structure, has special fragrance, close ester, low toxicity and physiologically active.Medicine containing ferrocene has been used for the treatment of anaemia, anti-inflammatory, antineoplastic field and demonstrate extraordinary effect; in order to obtain the compound of high biological activity and based on active principle of hybridization, research and develop the study hotspot that novel texture acyl Ferrocene thiadiazole compound has become this compounds.
The acyl Ferrocene contracting 2-amino-5-prepared in prior art replaces-1; 3; 4-thiadiazoles many employings liquid-phase reflux synthesis method; although successfully synthesized this product; but its temperature of reaction is higher, length consuming time, last handling process is complicated; be difficult in the industrial production realize producing in enormous quantities, synthesis technique is to be further improved in addition.
Summary of the invention
For problems of the prior art, the invention provides the method that one prepares acyl Ferrocene contracting 2-amino-5-replacement-1,3,4-thiadiazoles.The method is simple to operate, and the reaction times is short, and reaction conditions is gentle, and equipment requirements is low, and aftertreatment is simple, need not solvent, and catalyzer is reusable, and green, economy, environmental protection, efficiently, productive rate is high.
For achieving the above object, the present invention adopts following technical scheme:
One prepares the method that acyl Ferrocene contracting 2-amino-5-replaces-1,3,4-thiadiazoles, comprises the following steps:
1) in the reactor of drying, add A mol acyl Ferrocene, B mol 2-amino-5-replaces-1,3,4-thiadiazoles and C mol tosic acid, is ground to raw material complete reaction, obtains crude product under room temperature; Wherein A:B:C=1:(1.0 ~ 1.2): (1.0 ~ 1.2);
2) dried in an oven by crude product, after being then cooled to room temperature, add dissolution with solvents, suction filtration obtains filtrate, concentrates filtrate to dry, obtains crude product;
3) crude product solvent is carried out recrystallization, obtain acyl Ferrocene contracting 2-amino-5-and replace-1,3,4-thiadiazoles.
As a further improvement on the present invention, described acyl Ferrocene is ferrocene carboxaldehyde or ferrocenyl methyl ketone.
As a further improvement on the present invention, described 2-amino-5-replaces-1, 3, substituting group in 4-thiadiazoles comprises hydrogen base, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, n-pentyl, n-hexyl, dodecyl, n-heptadecane base, phenyl, Chloro-O-Phenyl, o-hydroxy-phenyl, to fluorine-based phenyl, adjacent fluorine-based phenyl, p-methylphenyl, p-nitrophenyl, o-methoxyphenyl, p-aminophenyl, 4-pyridyl, 2, 4-Dichlorophenoxy methylene radical, benzene Oxymethylene, to methylenedioxy phenoxy methylene radical, to anisole Oxymethylene, p-nitrophenyl Oxymethylene, to bromobenzene Oxymethylene, to chlorobenzene Oxymethylene.
As a further improvement on the present invention; described step 1) in detect at process of lapping TLC; represent raw material complete reaction when acyl Ferrocene raw material point disappears, the developping agent adopted during TLC detects is volume ratio is the ethyl acetate of 1:3 and the mixed solvent of sherwood oil.
As a further improvement on the present invention, described step 1) in grinding carry out in mortar, the time be ground to needed for raw material complete reaction is 15 ~ 30min.
As a further improvement on the present invention, step 2) in baking oven drying condition be 50 DEG C of insulation 30min.
As a further improvement on the present invention, step 2) and step 3) in solvent be dehydrated alcohol.
Compared with prior art, beneficial effect of the present invention is:
The present invention replaces-1,3,4-thiadiazoles for raw material with acyl Ferrocene, 2-amino-5-, and tosic acid is catalyzer, adopts solid-phase sequencing to prepare a series of acyl Ferrocene contracting 2-amino-5-and replaces-1,3,4-thiadiazoles.The method is simple to operate, and the reaction times is short, and reaction conditions is gentle, and equipment requirements is low, and aftertreatment is simple, need not solvent, and catalyzer is reusable, and green, economy, environmental protection, efficiently, productive rate is high.Solid-phase sequencing polishing is compared traditional methodology of organic synthesis and is had: the reaction times is short, and reaction conditions is gentle, and equipment requirements is low, and simple to operate, aftertreatment is simple, and without the need to solvent, productive rate advantages of higher is a kind of green, economy, environmental protection, efficient organic synthetic experiment method.Productive rate is up to more than 85%.
Further, the present invention removes catalyzer and recrystallization all uses dehydrated alcohol, removes catalyst effect good, and recrystallization uses unified solvent can not bring pollution to product again.
Further, the present invention's TLC monitoring reaction course used, ethyl acetate and the sherwood oil of developping agent used to be volume ratio be 1:3.Monitoring accurately, is beneficial to and controls extent of reaction and end.
Accompanying drawing explanation
Fig. 1 is ferrocenyl methyl ketone contracting 2-amido-1,3,4-thiadiazoles IR spectrogram;
Fig. 2 is ferrocenyl methyl ketone contracting 2-amino-5-sulfydryl-1,3,4-thiadiazoles IR spectrogram;
Fig. 3 is ferrocenyl methyl ketone contracting 2-amino-5-(4-pyridyl)-1,3,4-thiadiazoles IR spectrogram;
Fig. 4 is ferrocenyl methyl ketone contracting 2-amino-5-n-propyl-1,3,4-thiadiazoles 1h-NMR spectrogram;
Fig. 5 is ferrocenyl methyl ketone contracting 2-amino-5-sulfydryl-1,3,4-thiadiazoles 1h-NMR spectrogram;
Fig. 6 is ferrocenyl methyl ketone contracting 2-amino-5-(4-pyridyl)-1,3,4-thiadiazoles 1h-NMR spectrogram;
Fig. 7 is ferrocenyl methyl ketone contracting 2-amino-5-phenyl-1,3,4-thiadiazoles 1h-NMR spectrogram.
Embodiment
The present invention replaces-1,3,4-thiadiazoles for raw material with acyl Ferrocene, 2-amino-5-, and tosic acid is catalyzer, and reaction generates acyl Ferrocene contracting 2-amino-5-and replaces-1,3,4-thiadiazoles, and its reaction equation is such as formula shown in (1).
Wherein substituent R 1base is selected from hydrogen base and methyl;
Wherein substituent R 2base is selected from hydrogen base, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, n-pentyl, n-hexyl, dodecyl, n-heptadecane base, phenyl, Chloro-O-Phenyl, o-hydroxy-phenyl, to fluorine-based phenyl, adjacent fluorine-based phenyl, p-methylphenyl, p-nitrophenyl, o-methoxyphenyl, p-aminophenyl, 4-pyridyl, 2,4 dichloro benzene Oxymethylene, benzene Oxymethylene, to methylenedioxy phenoxy methylene radical, to anisole Oxymethylene, p-nitrophenyl Oxymethylene, to bromobenzene Oxymethylene, to chlorobenzene Oxymethylene.
Below in conjunction with specific embodiment, the present invention is described in further detail, and the explanation of the invention is not limited.
Embodiment 1
1) in the mortar of drying, 0.001mol ferrocene carboxaldehyde is added, 0.001mol 2-amino-5-methyl isophthalic acid, 3,4-thiadiazoles and 0.0012mol tosic acid, raw material reaction is ground to completely (TLC monitors reaction) under room temperature, time is 15min, then it is incubated 30min in an oven under 50 DEG C of conditions.
2) be then cooled to room temperature and add dehydrated alcohol, by mixed solution suction filtration, removing catalyzer tosic acid, filtrate reduced in volume, to dry, obtains crude product.Crude product dehydrated alcohol carries out recrystallization, obtains formylferrocene contracting 2-amino-5-methyl isophthalic acid, 3,4-thiadiazoles.
IR(KBr，v/cm -1)：3555，3473，2960，2933，1618，1455，1378，1377，1196，1196，1074，669，479；
1h-NMR:4.820 (m, 2H replace the H with C=N ortho position on luxuriant ring); 4.752 (m, 2H to replace on luxuriant ring and the H of position between C=N); 2.505 (vs, 6H, DMSO-d бsolvent).
Embodiment 2
1) in the mortar of drying, 0.001mol ferrocenyl methyl ketone is added; 0.001mol 2-amino-1; 3; 4-thiadiazoles and 0.0012mol tosic acid; raw material reaction is ground to completely (TLC monitors reaction) under room temperature; time is 20min, then it is incubated 30min in an oven under 50 DEG C of conditions.
2) be then cooled to room temperature and add dehydrated alcohol, by mixed solution suction filtration, removing catalyzer tosic acid, filtrate reduced in volume, to dry, obtains crude product.Crude product dehydrated alcohol carries out recrystallization, obtains ferrocenyl methyl ketone contracting 2-amido-1,3,4-thiadiazoles.
As seen from Figure 1,3301,3089cm -1for the C-H stretching vibration on ferrocene absorbs strong peak; 1504,1423cm -1for C=N stretching vibration absorbs strong peak; 825cm -1for the C-H stretching vibration on ferrocene absorbs weak peak; 490cm -1for N-C-S stretching vibration absorbs weak peak.IR(KBr，v/cm -1)：3301，3089，2923，1604，1504，1423，1375，1113，1024，825，490；
1h-NMR:8.60 (1H ,-H, unimodal), 4.47 (2H, Fc-H, multiplets), 2.03 (3H ,-CH 3, unimodal), 4.23 (5H, Fc-H, triplets).
Embodiment 3
1) in the mortar of drying, 0.001mol ferrocenyl methyl ketone is added; 0.001mol 2-amino-5-methyl isophthalic acid; 3; 4-thiadiazoles and 0.0012mol tosic acid; raw material reaction is ground to completely (TLC monitors reaction) under room temperature; time is 25min, then it is incubated 30min in an oven under 50 DEG C of conditions.
2) be then cooled to room temperature and add dehydrated alcohol, by mixed solution suction filtration, removing catalyzer tosic acid, filtrate reduced in volume, to dry, obtains crude product.Crude product dehydrated alcohol carries out recrystallization, obtains ferrocenyl methyl ketone contracting 2-amino-5-methyl isophthalic acid, 3,4-thiadiazoles.
IR(KBr，v/cm -1)：3426，2925，1605，1527，1427，1377，1104，1001，828，648，495；
1h-NMR:4.53-4.80 (2H, Fc-H, multiplet), 4.26 (5H, Fc-H, triplets), 2.05-2.52 (3H ,-CH 3, unimodal).
Embodiment 4
1) in the mortar of drying, 0.001mol ferrocenyl methyl ketone is added; 0.001mol 2-amino-5-ethyl-1; 3; 4-thiadiazoles and 0.0012mol tosic acid; raw material reaction is ground to completely (TLC monitors reaction) under room temperature; time is 28min, then it is incubated 30min in an oven under 50 DEG C of conditions.
2) be then cooled to room temperature and add dehydrated alcohol, by mixed solution suction filtration, removing catalyzer tosic acid, filtrate reduced in volume, to dry, obtains crude product.Crude product dehydrated alcohol carries out recrystallization, obtains ferrocenyl methyl ketone contracting 2-amino-5-ethyl-1,3,4-thiadiazoles.
IR(KBr，v/cm -1)：3426，2925，1605，1527，1427，1377，1104，1001，828，648，478；
1h-NMR:4.49-4.85 (2H, Fc-H, multiplet), 4.26 (5H, Fc-H, triplets), 2.79 (2H ,-CH 2-, multiplet), 2.09 (3H ,-CH 3, unimodal), 1.24 (3H ,-CH 3, triplet).
Embodiment 5
1) in the mortar of drying, 0.001mol ferrocenyl methyl ketone is added; 0.001mol 2-amino-5-n-propyl-1; 3; 4-thiadiazoles and 0.0012mol tosic acid; raw material reaction is ground to completely (TLC monitors reaction) under room temperature; time is 30min, then it is incubated 30min in an oven under 50 DEG C of conditions.
2) be then cooled to room temperature and add dehydrated alcohol, by mixed solution suction filtration, removing catalyzer tosic acid, filtrate reduced in volume, to dry, obtains crude product.Crude product dehydrated alcohol carries out recrystallization, obtains ferrocenyl methyl ketone contracting 2-amino-5-n-propyl-1,3,4-thiadiazoles.
IR(KBr，v/cm -1)：3423，3160，2926，1742，1673，1612，1526，1459，1097，1010，813，661，472；
As seen from Figure 4,0.96,2.06ppm is methyl proton peak; 1.63,2,93ppm is methene proton peak; 4.32,4.66,4.97ppm is ferrocene proton peak. 1h-NMR:4.66-4.97 (2H, Fc-H, multiplet), 4.32 (5H, Fc-H, triplets), 2.93 (2H ,-CH 2-, triplet), 2.06 (3H ,-CH 3, unimodal), 1.63 (2H ,-CH 2-, multiplet), 0.96 (3H ,-CH 3, triplet).
Embodiment 6
1) in the mortar of drying, 0.001mol ferrocenyl methyl ketone is added; 0.001mol 2-amino-5-sulfydryl-1; 3; 4-thiadiazoles and 0.0012mol tosic acid; raw material reaction is ground to completely (TLC monitors reaction) under room temperature; time is 15min, then it is incubated 30min in an oven under 50 DEG C of conditions.
2) be then cooled to room temperature and add dehydrated alcohol, by mixed solution suction filtration, removing catalyzer tosic acid, filtrate reduced in volume, to dry, obtains crude product.Crude product dehydrated alcohol carries out recrystallization, obtains ferrocenyl methyl ketone contracting 2-amino-5-sulfydryl-1,3,4-thiadiazoles.
As seen from Figure 2,3294,3177cm -1for the C-H stretching vibration on ferrocene absorbs strong peak; 1559,1507cm -1for C=N stretching vibration absorbs strong peak; 825cm -1for the C-H stretching vibration on ferrocene absorbs weak peak; 621,484cm -1for N-C-S stretching vibration absorbs weak peak.IR(KBr，v/cm -1)：3294，3177，2925，1617，1559，1507，1375，1032，825，621，484；
As seen from Figure 5,2.10ppm is methyl proton peak; 4.20,4.64,4.91ppm is ferrocene proton peak; 7.22ppm is N-H proton peak. 1h-NMR:7.22 (1H, N-H, unimodal), 4.64-4.91 (2H, Fc-H, multiplet), 4.20 (5H, Fc-H, triplets), 2.10 (3H ,-CH 3, unimodal).
Embodiment 7
1) in the mortar of drying, 0.001mol ferrocenyl methyl ketone is added; 0.001mol 2-amino-5-(4-pyridyl)-1; 3; 4-thiadiazoles and 0.0012mol tosic acid; raw material reaction is ground to completely (TLC monitors reaction) under room temperature; time is 15min, then it is incubated 30min in an oven under 50 DEG C of conditions.
2) be then cooled to room temperature and add dehydrated alcohol, by mixed solution suction filtration, removing catalyzer tosic acid, filtrate reduced in volume, to dry, obtains crude product.Crude product dehydrated alcohol carries out recrystallization, obtains ferrocenyl methyl ketone contracting 2-amino-5-(4-pyridyl)-1,3,4-thiadiazoles.
As seen from Figure 3,3295cm -1for the C-H stretching vibration on ferrocene absorbs strong peak; 3089,745cm -1for pyridine ring skeleton; 1611cm -1for the C=N stretching vibration on Schiff absorbs strong peak; 603,431cm -1for N-C-S stretching vibration absorbs weak peak.IR(KBr，v/cm -1)：3295，3089，2866，2775，1611，1498，1106，1002，804，603，431；
As seen from Figure 6,2.07ppm is methyl proton peak; 4.12,4.52,4.78ppm is ferrocene proton peak; 7.92,8.22ppm pyridine proton peak. 1h-NMR:7.92-8.22 (4H, pyridy-H, multiplet), 4.52-4.78 (2H, Fc-H, multiplet), 4.12 (5H, Fc-H, triplets), 2.07 (3H ,-CH 3, unimodal).
Embodiment 8
1) in the mortar of drying, 0.001mol ferrocenyl methyl ketone is added; 0.001mol 2-amino-5-phenyl-1; 3; 4-thiadiazoles and 0.0012mol tosic acid; raw material reaction is ground to completely (TLC monitors reaction) under room temperature; time is 20min, then it is incubated 30min in an oven under 50 DEG C of conditions.
2) be then cooled to room temperature and add dehydrated alcohol, by mixed solution suction filtration, removing catalyzer tosic acid, filtrate reduced in volume, to dry, obtains crude product.Crude product dehydrated alcohol carries out recrystallization, obtains ferrocenyl methyl ketone contracting 2-amino-5-phenyl-1,3,4-thiadiazoles.
IR(KBr，v/cm -1)：3292，3089，3036，2917，1617，1547，1501，1461，1112，1046，806，643，486；
As seen from Figure 7,2.05ppm is methyl proton peak; 4.17,4.37,4.62ppm is ferrocene proton peak; 7.72,7.96,8.06ppm is benzene proton peak. 1h-NMR:7.72-8.06 (5H, Ph-H, multiplet), 4.37-4.62 (2H, Fc-H, multiplet), 4.17 (5H, Fc-H, triplets), 2.05 (3H ,-CH 3, unimodal).

Claims (7)

1. the method prepared acyl Ferrocene contracting 2-amino-5-and replace-1,3,4-thiadiazoles, is characterized in that, comprise the following steps:
1) in the reactor of drying, add A mol acyl Ferrocene, B mol 2-amino-5-replaces-1,3,4-thiadiazoles and C mol tosic acid, is ground to raw material complete reaction, obtains crude product under room temperature; Wherein A:B:C=1:(1.0 ~ 1.2): (1.0 ~ 1.2);
2) dried in an oven by crude product, after being then cooled to room temperature, add dissolution with solvents, suction filtration obtains filtrate, concentrates filtrate to dry, obtains crude product;
3) crude product solvent is carried out recrystallization, obtain acyl Ferrocene contracting 2-amino-5-and replace-1,3,4-thiadiazoles.
2. one according to claim 1 prepares the method that acyl Ferrocene contracting 2-amino-5-replaces-1,3,4-thiadiazoles, it is characterized in that: described acyl Ferrocene is ferrocene carboxaldehyde or ferrocenyl methyl ketone.
3. the acyl Ferrocene contracting 2-amino-5-for preparing according to claim 1 and 2 replaces-1, 3, the method of 4-thiadiazoles, it is characterized in that: described 2-amino-5-replaces-1, 3, substituting group in 4-thiadiazoles comprises hydrogen base, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, n-pentyl, n-hexyl, dodecyl, n-heptadecane base, phenyl, Chloro-O-Phenyl, o-hydroxy-phenyl, to fluorine-based phenyl, adjacent fluorine-based phenyl, p-methylphenyl, p-nitrophenyl, o-methoxyphenyl, p-aminophenyl, 4-pyridyl, 2, 4-Dichlorophenoxy methylene radical, benzene Oxymethylene, to methylenedioxy phenoxy methylene radical, to anisole Oxymethylene, p-nitrophenyl Oxymethylene, to bromobenzene Oxymethylene, to chlorobenzene Oxymethylene.
4. the acyl Ferrocene contracting 2-amino-5-for preparing according to claim 1 replaces-1; 3; the method of 4-thiadiazoles; it is characterized in that: described step 1) in detect at process of lapping TLC; represent raw material complete reaction when acyl Ferrocene raw material point disappears, the developping agent adopted during TLC detects is volume ratio is the ethyl acetate of 1:3 and the mixed solvent of sherwood oil.
5. the method for preparation 2-amino-5-alkyl-1,3,4-thiadiazoles according to claim 1, is characterized in that: described step 1) in grinding carry out in mortar, the time be ground to needed for raw material complete reaction is 15 ~ 30min.
6. the method prepared acyl Ferrocene contracting 2-amino-5-and replace-1,3,4-thiadiazoles according to claim 1, is characterized in that: step 2) and step 3) in solvent be dehydrated alcohol.
7. the method prepared acyl Ferrocene contracting 2-amino-5-and replace-1,3,4-thiadiazoles according to claim 1, is characterized in that: step 2) in baking oven drying condition be 50 DEG C of insulation 30min.
CN201510026286.5A 2015-01-19 2015-01-19 Method for preparing carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole Pending CN104558057A (en)

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CN110294781A (en) * 2019-07-25 2019-10-01 陕西科技大学 One kind Schiff of thiadiazolyl group containing ferrocenyl and preparation method thereof
CN113066992A (en) * 2021-03-08 2021-07-02 常州大学 Alkaline aqueous single flow battery based on double-metal MOF positive electrode and organic matter negative electrode
CN115043886A (en) * 2022-06-22 2022-09-13 广西民族大学 Ferrocenamide derivative and synthesis method and application thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110294781A (en) * 2019-07-25 2019-10-01 陕西科技大学 One kind Schiff of thiadiazolyl group containing ferrocenyl and preparation method thereof
CN110294781B (en) * 2019-07-25 2022-04-12 陕西科技大学 Schiff base containing ferrocenyl thiadiazole base and preparation method thereof
CN113066992A (en) * 2021-03-08 2021-07-02 常州大学 Alkaline aqueous single flow battery based on double-metal MOF positive electrode and organic matter negative electrode
CN113066992B (en) * 2021-03-08 2022-06-17 常州大学 Alkaline aqueous single flow battery based on double-metal MOF positive electrode and organic matter negative electrode
CN115043886A (en) * 2022-06-22 2022-09-13 广西民族大学 Ferrocenamide derivative and synthesis method and application thereof

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