CN110294781A - One kind Schiff of thiadiazolyl group containing ferrocenyl and preparation method thereof - Google Patents
One kind Schiff of thiadiazolyl group containing ferrocenyl and preparation method thereof Download PDFInfo
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- CN110294781A CN110294781A CN201910676424.2A CN201910676424A CN110294781A CN 110294781 A CN110294781 A CN 110294781A CN 201910676424 A CN201910676424 A CN 201910676424A CN 110294781 A CN110294781 A CN 110294781A
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Abstract
The choline chloride of A mol is added into dry three-necked flask, eutectic solvent is stirred at room temperature to obtain in the methanesulfonic acid of B mol; then C mol ferrocenyl methyl ketone is added, D mol 2- amino -5- replaces -1,3; 4- thiadiazoles, 40 DEG C of water-bath are reacted, and TLC is monitored until the reaction is complete.After reaction, reaction solution is poured into water, is extracted with dichloromethane, solvent afforded crude material is evaporated off, water phase is recovered to regain eutectic solvent.Crude product recrystallizes to obtain the sterling Schiff of thiadiazolyl group containing ferrocenyl through dehydrated alcohol.Operation of the present invention is simple, and yield is high, and product purity is high, and the reaction time is short, and post-processing is simple, and eutectic solvent can be recycled and be recycled, environmentally protective, low in cost, has great importance to the synthesis and development of such compound.
Description
Technical field
The invention belongs to the field of chemical synthesis, the in particular to Schiff of thiadiazolyl group containing ferrocenyl and its preparation side
Method.
Background technique
Schiff has very strong physiological activity and prevents the activity of fungus growth, may be used as antibacterial, anticancer, resists and swell
The drug of tumor, treating tuberculosis etc.；And the complex that Schiff class compound and metal are formed also has fairly good oxygen carrier living
Property；Schiff and its complex also have good catalytic activity simultaneously, can be in asymmetric syntheses and Polymer Synthesizing
As catalyst.Ferrocene and heterocyclic amine are introduced into compound simultaneously, synthesize the Schiff of thiadiazolyl group containing ferrocenyl, it will
A new hot spot as Schiff research from now on.
Traditional Schiff synthetic method uses Lewis acid as catalyst, and dehydrated alcohol makees solvent, and return time is long,
Reaction temperature is high, low yield and not environmentally, so developing a kind of easy to operate, yield is high, environmentally protective, low-cost system
The method of the standby Schiff of thiadiazolyl group containing ferrocenyl has definite meaning.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation method of Schiff of thiadiazolyl group containing ferrocenyl, this method tools
There is easy to operate, yield is high, product purity is high, the reaction time is short, eutectic solvent is recyclable to be recycled, it is environmentally protective, at
This cheap advantage.
In order to achieve the above objectives, the technical solution adopted by the present invention are as follows:
The general structure of the Schiff of thiadiazolyl group containing ferrocenyl are as follows:
Wherein, R is-H ,-CH3,-C2H5,-C3H7- n ,-SH,,,,,,,,,,,,,,。
The preparation method of the Schiff of thiadiazolyl group containing ferrocenyl, comprising the following steps:
The choline chloride of A mol is added into dry three-necked flask, it is molten that obtained eutectic is stirred at room temperature in the methanesulfonic acid of B mol
Then C mol ferrocenyl methyl ketone is added in agent, D mol 2- amino -5- replaces -1,3,4- thiadiazoles, and 40 DEG C of water-bath carry out instead
It answers, TLC is monitored until the reaction is complete.After reaction, reaction solution is poured into water, is extracted with dichloromethane, solvent is evaporated off and obtains
Crude product, water phase is recovered to regain eutectic solvent.Crude product recrystallizes to obtain sterling thiophene containing ferrocenyl two through dehydrated alcohol
Oxazolyl Schiff.
The general structure of the ferrocenyl methyl ketone is as follows:
The general structure of the 2- amino 5- substitution -1,3,4- thiadiazoles is as follows:
Wherein, R is-H ,-CH3,-C2H5,-C3H7- n ,-SH,,,,,,,,,,,,,,。
The TLC monitoring, the solvent used is the mixed liquor of the petroleum ether that volume ratio is 5:1 and ethyl acetate.
Compared with the existing technology, the invention has the benefit that
The preparation method of the Schiff of thiadiazolyl group containing ferrocenyl provided by the invention, with ferrocenyl methyl ketone, 2- amino -5-
- 1,3,4- thiadiazoles of substitution are raw material, and eutectic solvent choline chloride-methanesulfonic acid, can high yield as solvent and catalyst
Be made the Schiff of thiadiazolyl group containing ferrocenyl.This method is easy to operate, yield is high, product purity is high, the reaction time is short,
Eutectic solvent is recyclable to be recycled, environmentally protective, low in cost, is had great application prospect.
Detailed description of the invention
Fig. 1 is the IR spectrogram of ferrocenyl methyl ketone contracting 2- amino -1,3,4- thiadiazoles Schiff prepared by embodiment 1
Fig. 2 is ferrocenyl methyl ketone contracting 2- amino -5- methyl-1 prepared by embodiment 2, the IR of 3,4- thiadiazoles Schiff
Spectrogram
Fig. 3 is the IR of ferrocenyl methyl ketone contracting 2- amino -5- ethyl -1,3,4- thiadiazoles Schiff prepared by embodiment 3
Spectrogram
Fig. 4 is ferrocenyl methyl ketone contracting 2- amino -5- n-propyl -1,3,4- thiadiazoles Schiff prepared by embodiment 4
IR spectrogram
Fig. 5 is the IR of ferrocenyl methyl ketone contracting 2- amino -5- sulfydryl -1,3,4- thiadiazoles Schiff prepared by embodiment 5
Spectrogram
Fig. 6 is ferrocenyl methyl ketone contracting 2- amino -5- (4- pyridyl group) -1,3,4- thiadiazoles Schiff prepared by embodiment 6
The IR spectrogram of alkali
Fig. 7 is the IR of ferrocenyl methyl ketone contracting 2- amino-5-phenyl -1,3,4- thiadiazoles Schiff prepared by embodiment 7
Spectrogram
Fig. 8 is ferrocenyl methyl ketone contracting 2- amino -1,3,4- thiadiazoles Schiff prepared by embodiment 11H NMR spectra
Fig. 9 is ferrocenyl methyl ketone contracting 2- amino -5- methyl-1 prepared by embodiment 2,3,4- thiadiazoles Schiff1H
NMR spectra
Figure 10 is ferrocenyl methyl ketone contracting 2- amino -5- ethyl -1,3,4- thiadiazoles Schiff prepared by embodiment 31H
NMR spectra
Figure 11 is ferrocenyl methyl ketone contracting 2- amino -5- n-propyl -1,3,4- thiadiazoles Schiff prepared by embodiment 4
's1H NMR spectra
Figure 12 is ferrocenyl methyl ketone contracting 2- amino -5- sulfydryl -1,3,4- thiadiazoles Schiff prepared by embodiment 51H
NMR spectra
Figure 13 is ferrocenyl methyl ketone contracting 2- amino -5- (4- pyridyl group) -1,3,4- thiadiazoles Schiff prepared by embodiment 6
Alkali1H NMR spectra
Figure 14 is ferrocenyl methyl ketone contracting 2- amino-5-phenyl -1,3,4- thiadiazoles Schiff prepared by embodiment 71H
NMR spectra.
Specific embodiment
It is that example is combined to be described in further details the present invention below:
The present invention is to replace -1,3,4- thiadiazoles for raw material with ferrocenyl methyl ketone, 2- amino -5-, eutectic solvent chlorination gallbladder
Alkali-methanesulfonic acid prepares a series of Schiffs of thiadiazolyl group containing ferrocenyl as solvent and catalyst.Its reactional equation
Formula is as follows:
Wherein R is H, CH3, C2H5, C3H7- n(n-propyl), SH,,
The preparation of 1 ferrocenyl methyl ketone contracting 2- amino -1,3,4- thiadiazoles Schiff of embodiment:
The choline chloride of 1.4g (10mmol), the methanesulfonic acid of 1.92 (20mmol) are added into dry three-necked flask, room temperature is stirred
Mixing obtains eutectic solvent, then addition 0.23g (1mmol) ferrocenyl methyl ketone, 0.12g (1.2mmol) 2- amino -1,3,
4- thiadiazoles, 40 DEG C of water-bath are reacted, and TLC is monitored until the reaction is complete.After reaction, reaction solution is poured into water, is used
Methylene chloride extraction, is evaporated off solvent afforded crude material, water phase is recovered to regain eutectic solvent.Crude product is tied again through dehydrated alcohol
It is brilliant to obtain sterling thiadiazolyl group containing ferrocenyl Schiff.Yield 94.2%, 148~149 DEG C of fusing point.
IR(KBr) ν: 3301cm-1,3089cm-1(ν Ferrocene C-H); 2923cm-1 (ν CH3); 1375cm-1(ν CH3) ;
1604cm-1(ν C=N);1504cm-1,1423cm-1 (ν Thiadiazole);1113cm-1 (ν C-S-C); 825cm-1 (ν Ferrocene C-H) ;
490cm-1 (ν N-C-S) ;
1H NMR(400 MHz, DMSO-d6) δ: 2.03(3H,-CH3, unimodal), 4.23 (5H, Fc-H, triplets), 4.47
(2H, Fc-H, multiplet), 4.79 (2H, Fc-H, multiplets), 8.60 (1H ,-H, unimodal).
2 ferrocenyl methyl ketone contracting 2- amino -5- methyl-1 of embodiment, the preparation of 3,4- thiadiazoles Schiff
The choline chloride of 1.4g (10mmol), the methanesulfonic acid of 1.92 (20mmol) are added into dry three-necked flask, room temperature is stirred
Mixing obtains eutectic solvent, and 0.23g (1mmol) ferrocenyl methyl ketone, 0.14g (1.2mmol) 2- amino -5- first is then added
Base -1,3,4- thiadiazoles, 40 DEG C of water-bath are reacted, and TLC is monitored until the reaction is complete.After reaction, reaction solution is poured into
It in water, is extracted with dichloromethane, solvent afforded crude material is evaporated off, water phase is recovered to regain eutectic solvent.Crude product is through anhydrous
Ethyl alcohol recrystallization obtains the sterling Schiff of thiadiazolyl group containing ferrocenyl.Yield 90.3%, 150~152 DEG C of fusing point.
IR(KBr) ν: 3426cm-1 (ν FerroceneC-H); 2925cm-1 (ν CH3); 1377cm-1 (ν CH3) ; 1605cm-1
(ν C=N); 1527cm-1,1427cm-1 (ν Thiadiazole); 1104cm-1 (ν C-S-C); 828cm-1,(ν FerroceneC-H); 648 cm-1,
495cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) δ: 2.05(3H,-CH3, unimodal), 2.51 (3H ,-CH3, unimodal),
4.26 (5H, Fc-H, triplets), 4.53 (2H, Fc-H, multiplets), 4.80 (2H, Fc-H, multiplets).
The preparation of 3 ferrocenyl methyl ketone contracting 2- amino -5- ethyl -1,3,4- thiadiazoles Schiff of embodiment
The choline chloride of 1.4g (10mmol), the methanesulfonic acid of 1.92 (20mmol) are added into dry three-necked flask, room temperature is stirred
Mixing obtains eutectic solvent, and 0.23g (1mmol) ferrocenyl methyl ketone, 0.15g (1.2mmol) 2- amino -5- second is then added
Base -1,3,4- thiadiazoles, 40 DEG C of water-bath are reacted, and TLC is monitored until the reaction is complete.After reaction, reaction solution is poured into
It in water, is extracted with dichloromethane, solvent afforded crude material is evaporated off, water phase is recovered to regain eutectic solvent.Crude product is through anhydrous
Ethyl alcohol recrystallization obtains the sterling Schiff of thiadiazolyl group containing ferrocenyl.Yield 91.7%, 145~146 DEG C of fusing point.
IR(KBr) ν: 3291cm-1,3114cm-1 (ν FerroceneC-H); 2928cm-1 (ν CH3); 1742cm-1, 1380cm-1(ν CH3); 1618cm-1 (ν C=N,s); 1526cm-1,1458cm-1 (ν Thiadiazole); 1112cm-1 (ν C-S-C); 787cm-1
(ν FerroceneC-H); 694 cm-1,478cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) δ: 1.24(3H,-CH3, triplet), 2.09 (3H ,-CH3, unimodal),
2.79(2H,-CH2, multiplet), 4.26 (5H, Fc-H, triplets), 4.49 (2H, Fc-H, multiplets), 4.85 (2H,
Fc-H, multiplet).
The preparation of 4 ferrocenyl methyl ketone contracting 2- amino -5- n-propyl -1,3,4- thiadiazoles Schiff of embodiment
The choline chloride of 1.4g (10mmol), the methanesulfonic acid of 1.92 (20mmol) are added into dry three-necked flask, room temperature is stirred
Mixing obtains eutectic solvent, 0.23g (1mmol) ferrocenyl methyl ketone is then added, 0.17g (1.2mmol) 2- amino -5- is just
Propyl -1,3,4- thiadiazoles, 40 DEG C of water-bath are reacted, and TLC is monitored until the reaction is complete.After reaction, reaction solution is fallen
Enter in water, be extracted with dichloromethane, solvent afforded crude material is evaporated off, water phase is recovered to regain eutectic solvent.Crude product is through nothing
Water-ethanol recrystallizes to obtain the sterling Schiff of thiadiazolyl group containing ferrocenyl.Yield 97.2%, 164~168 DEG C of fusing point.
IR(KBr) ν: 3423cm-1,3160cm-1 (ν FerroceneC-H);2926cm-1 (ν CH3);1612cm-1 (ν C=N) ;
1526cm-1,1459cm-1 (ν Thiadiazole); 1097cm-1,1010 cm-1 (ν C-S-C);813cm-1 (ν FerroceneC-H) ;661 cm-1,
472cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) δ:0.96(3H,-CH3, triplet), 1.63 (2H ,-CH2, multiple
Peak), 2.06 (3H ,-CH3, unimodal), 2.93 (2H ,-CH2, triplet), 4.32 (5H, Fc-H, triplets), 4.66 (2H,
Fc-H, multiplet), 4.97 (2H, Fc-H, multiplets).
The preparation of 5 ferrocenyl methyl ketone contracting 2- amino -5- sulfydryl -1,3,4- thiadiazoles Schiff of embodiment
The choline chloride of 1.4g (10mmol), the methanesulfonic acid of 1.92 (20mmol) are added into dry three-necked flask, room temperature is stirred
Mixing obtains eutectic solvent, and 0.23g (1mmol) ferrocenyl methyl ketone, the 2- amino -5- mercapto of 0.16 (1.2mmol) is then added
Base -1,3,4- thiadiazoles, 40 DEG C of water-bath are reacted, and TLC is monitored until the reaction is complete.After reaction, reaction solution is poured into
It in water, is extracted with dichloromethane, solvent afforded crude material is evaporated off, water phase is recovered to regain eutectic solvent.Crude product is through anhydrous
Ethyl alcohol recrystallization obtains the sterling Schiff of thiadiazolyl group containing ferrocenyl.Yield 94.1%, 161~164 DEG C of fusing point.
IR(KBr) ν: 3294cm-1,3177cm-1 (ν FerroceneC-H);2925cm-1 (ν CH3);1375cm-1 (ν CH3);
1617cm-1 (ν C=N);1559cm-1,1507cm-1 (ν Thiadiazole); 1105cm-1(ν C-S-C); 825cm-1 (ν FerroceneC-H); 621
cm-1,484cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) δ:2.10(3H,-CH3, unimodal), 4.20 (5H, Fc-H, triplets),
4.64 (2H, Fc-H, multiplets), 4.91 (2H, Fc-H, multiplets), 7.22 (1H, N-H, unimodal).
The preparation of embodiment 6 ferrocenyl methyl ketone contracting 2- amino -5- (4- pyridyl group) -1,3,4- thiadiazoles Schiff
The choline chloride of 1.4g (10mmol), the methanesulfonic acid of 1.92 (20mmol) are added into dry three-necked flask, room temperature is stirred
Mixing obtains eutectic solvent, and 0.23g (1mmol) ferrocenyl methyl ketone, 0.21g (1.2mmol) 2- amino -5- (4- is then added
Pyridyl group) -1,3,4- thiadiazoles, 40 DEG C of water-bath are reacted, and TLC is monitored until the reaction is complete.After reaction, by reaction solution
It is poured into water, is extracted with dichloromethane, solvent afforded crude material is evaporated off, water phase is recovered to regain eutectic solvent.Crude product warp
Dehydrated alcohol recrystallizes to obtain the sterling Schiff of thiadiazolyl group containing ferrocenyl.Yield 96.9%, 196~199 DEG C of fusing point.
IR(KBr) ν: 3295cm-1(ν FerroceneC-H);3089cm-1,745 cm-1 (ν Pyridine ring ) ;2775cm-1
(ν C thiadiazoles-C pyridine); 2866cm-1(ν CH3) ; 1283cm-1 (ν CH3);1611cm-1 (ν C=N,s);1523cm-1,1498cm-1,
(ν C=N); 1106cm-1(ν C-S-C); 804cm-1 (ν FerroceneC-H) ; 603 cm-1,431cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) δ: 2.07 (3H ,-CH3, unimodal), 4.12 (5H, Fc-H, triplets),
4.52 (2H, Fc-H, multiplets), 4.78 (2H, Fc-H, multiplets), 7.92,8.22, (4H, pyridy-H, it is multiple
Peak).
The preparation of 7 ferrocenyl methyl ketone contracting 2- amino-5-phenyl -1,3,4- thiadiazoles Schiff of embodiment
The choline chloride of 1.4g (10mmol), the methanesulfonic acid of 1.92 (20mmol) are added into dry three-necked flask, room temperature is stirred
Mixing obtains eutectic solvent, and 0.23g (1mmol) ferrocenyl methyl ketone, 0.21g (1.2mmol) 2- amino -5- benzene is then added
Base -1,3,4- thiadiazoles, 40 DEG C of water-bath are reacted, and TLC is monitored until the reaction is complete.After reaction, reaction solution is poured into
It in water, is extracted with dichloromethane, solvent afforded crude material is evaporated off, water phase is recovered to regain eutectic solvent.Crude product is through anhydrous
Ethyl alcohol recrystallization obtains the sterling Schiff of thiadiazolyl group containing ferrocenyl.Yield 96.8%, 182~184 DEG C of fusing point.
IR(KBr) ν: 3292cm-1 (ν FerroceneC-H);3089cm-1 (ν N-H); 3036cm-1 (ν Phenyl ring C-H ); 2917cm-1
(ν C thiadiazoles-C benzene) ; 1461cm-1 (ν CH3); 1617cm-1, (ν C=N)1547cm-1,1501cm-1,(ν C=N); 1112cm-1
(ν C-S-C); 806cm-1 (ν FerroceneC-H); 643 cm-1,486cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) δ:2.05(3H,-CH3, unimodal), 4.17 (5H, Fc-H, triplets),
4.37 (2H, Fc-H, multiplets), 4.62 (2H, Fc-H, multiplets), 7.72,7.96,8.06, (5H, Ph-H, multiplet).
8 water phase of embodiment can regain eutectic solvent through distillation.With ferrocenyl methyl ketone contracting 2- amino-5-phenyl-
For 1,3,4- thiadiazoles Schiff, the influence that eutectic solvent is recycled to ultimate yield is probed into, the results are shown in Table 1.
The influence to yield is recycled in 1 eutectic solvent of table
| Cycle-index | Yield (%) |
| 1 | 96.8 |
| 2 | 96.2 |
| 3 | 95.5 |
| 4 | 94.7 |
| 5 | 93.3 |
The result shows that eutectic solvent, which is recycled five times, does not have large effect to yield, still there is good urge to reaction
Change effect, illustrates that this method is simple and efficient and environmentally protective.
Claims (8)
1. a kind of Schiff of thiadiazolyl group containing ferrocenyl, which is characterized in that structural formula are as follows:
(I)；
Wherein, R is-H ,-CH3,-C2H5,-n-C3H7,-SH,,,,,,,,,,,,,,。
2. a kind of preparation method of the Schiff of thiadiazolyl group containing ferrocenyl, which comprises the steps of:
Ferrocenyl methyl ketone and 2- amino -5- replace -1,3,4- thiadiazoles anti-in choline chloride-methanesulfonic acid eutectic solvent
It answers, obtains ferrocenyl thiadiazolyl group Schiff.
3. a kind of preparation method of Schiff of thiadiazolyl group containing ferrocenyl according to claim 2, which is characterized in that
The 2- amino 5- replaces the general structure of -1,3,4- thiadiazoles are as follows:
(II)；
Wherein, R is-H ,-CH3,-C2H5,-n-C3H7,-SH,,,,,,,,,,,,,,。
4. a kind of preparation method of Schiff of thiadiazolyl group containing ferrocenyl according to claim 2, which is characterized in that
Reaction equation are as follows:
(III)；
Wherein, R is-H ,-CH3,-C2H5,-n-C3H7,-SH,,,,,,,,,,,,,,。
5. a kind of preparation method of Schiff of thiadiazolyl group containing ferrocenyl according to claim 2, which is characterized in that
Choline chloride-methanesulfonic acid eutectic solvent is by choline chloride and methanesulfonic acid 1:(1 ~ 2 in molar ratio) it is sufficiently mixed.
6. a kind of preparation method of Schiff of thiadiazolyl group containing ferrocenyl according to claim 2, which is characterized in that
Ferrocenyl methyl ketone is to replace the molar ratio of -1,3,4- thiadiazoles to be 1:(1.1 ~ 1.2 with 2- amino -5-).
7. a kind of preparation method of Schiff of thiadiazolyl group containing ferrocenyl according to claim 2, which is characterized in that
Specific step is as follows:
The choline chloride of A mol is added into dry three-necked flask, it is molten that obtained eutectic is stirred at room temperature in the methanesulfonic acid of B mol
Then C mol ferrocenyl methyl ketone is added in agent, D mol 2- amino -5- replaces -1,3,4- thiadiazoles, and 40 DEG C of water-bath carry out instead
It answers, TLC is monitored until the reaction is complete；After reaction, reaction solution is poured into water, is extracted with dichloromethane, solvent is evaporated off and obtains
Crude product, water phase is recovered to regain eutectic solvent；Crude product recrystallizes to obtain sterling thiophene containing ferrocenyl two through dehydrated alcohol
Oxazolyl Schiff.
8. a kind of preparation method of Schiff of thiadiazolyl group containing ferrocenyl according to claim 7, which is characterized in that
The TLC monitors reaction, when raw material point disappears, that is, fully reacting, and the solvent of the TLC is the stone that volume ratio is 5:1
The mixed liquor of oily ether and ethyl acetate.
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