CN105254530A - Method for synthesizing Schiff base compound containing camphenyl - Google Patents
Method for synthesizing Schiff base compound containing camphenyl Download PDFInfo
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- CN105254530A CN105254530A CN201510662580.5A CN201510662580A CN105254530A CN 105254530 A CN105254530 A CN 105254530A CN 201510662580 A CN201510662580 A CN 201510662580A CN 105254530 A CN105254530 A CN 105254530A
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- amphene
- aromatic amine
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Abstract
The invention discloses a method for synthesizing a Schiff base compound containing camphenyl. The method includes the following specific synthetic steps that camphorenal is used as a raw material, an aromatic amine compound is added in a reaction device containing organic solvent, the camphorenal and aromatic amine are fed according to the molar ratio of 1:1-1.1, stirring reflux is conducted for 2-3 hours, a reacted product is purified through solvent, and then drying is carried out, so that the Schiff base compound containing the camphenyl is obtained. According to the preparation method, the camphorenal is used as the raw material to be reacted with the aromatic amine compound so that the Schiff base compound can be obtained, camphene radicals are introduced into Schiff base, and finally the aromatic amine Schiff base containing the camphenyl is obtained. The experimental steps are simple and convenient, the reaction condition is moderate, time is short, the yield is high, safety and environmental protection are achieved, aftertreatment is convenient, and secondary pollution is small.
Description
Technical field
The present invention relates to compou nd synthesis technical field, specifically a kind of synthetic method containing amphene base Schiff compounds.
Background technology
Organic amine compound majority all has certain biological activity, but also can as intermediates such as synthesizing amide, schiff bases, quaternary ammonium salts.Schiff is the compound that a class has C=N structure, within 1864, is synthesized first by H.Schiff, its simple synthetic method, and can provide lone electron pair, can with metal as iron, cobalt, nickel, copper etc. and rare earth metal etc. form title complex.(Institutes Of Chifeng's journal (natural science edition), 2013,29 (11): 16-17.) research finds that Schiff and title complex thereof all have important application in pharmacy, catalysis, analytical chemistry, burn into liquid crystal material and the field such as photochromic; At medical field, Schiff derivative has antibacterial, sterilization, antitumor, antiviral biological activity.Therefore, be subject to the long-term attention of people, become one of popular research field.
On the other hand, amphene is a kind of bicyclic diterpene vinyl compound, and exist with multiple natural volatile oil, as white oil of camphor, pamorusa oil, turps and cypress wet goods, being the renewable raw materials of Fine Chemical, is again one of Main By product in turps deep processing.Amphene is mainly used in organic synthesis raw material, can be used for the raw material as medicine moiety and synthetic essence and flavoring agent such as medicine, makeup and food service industry, itself also can be used as the weighting agent (JournaloftheAmericanCeramicSociety preparing novel porous materials, 2012,95 (6): 1803 ~ 1806.).All actual application value is had in industries such as fine chemistry industry, medicine, food, materials by the derivative of its synthesis.In recent years, chemically modified synthesis is carried out for the structure of natural chemicals there is bioactive compound to have become one of study hotspot of chemistry of forest product and Synthetic Organic Chemistry.
In the numerous derivatives synthesized by amphene, good purposes is had in essence and flavoring agent industry, but the application report in other industry is few, in order to carry out deep screening active ingredients and this applied research relevant thereof to camphene derivatives, be necessary the kind and the quantity that increase this compounds.At present, the described synthetic method containing amphene base Schiff compounds is not still had.Therefore, the present invention has probed into 9 kinds of synthetic methods containing amphene base Schiff compounds, and determines general synthetic method.
Summary of the invention
The object of the present invention is to provide a kind of synthetic method containing amphene base Schiff compounds, to solve the problem proposed in above-mentioned background technology.
For achieving the above object, the invention provides following technical scheme:
A synthetic method containing amphene base Schiff compounds, concrete synthesis step is as follows:
(1) with amphene aldehyde for raw material, aromatic amine compounds is added at the reaction unit of organic solvent, amphene aldehyde and aromatic amine are 1: 1 ~ 1.1 to feed intake in molar ratio, stirring and refluxing 2 ~ 3h, and gas phase follows the tracks of extent of reaction till target product content no longer increases;
(2) benzene in above-mentioned reaction solution or cyclohexane solvent are steamed, the thick product solvent obtained carries out purifying, then carries out drying, and obtain amphene base Schiff compounds, its reaction formula is:
Wherein, R is the substituting group of different positions on phenyl ring.
As the further scheme of the present invention: described aromatic amine includes but not limited to aniline or substituted aniline.
As the further scheme of the present invention: described substituted aniline includes but not limited to Ortho Toluidine, para-totuidine, para-bromoaniline, Ortho-Chloro aniline, p-Chlorobenzoic acid amide, P-nethoxyaniline, m-nitraniline, p-Nitroaniline.
As the further scheme of the present invention: described organic solvent is benzene or cyclohexane.
As the further scheme of the present invention: described reaction unit is the reaction unit with water trap.
As the present invention's further scheme: solvent that this purifying uses is methyl alcohol or ethanol.
Compared with prior art, the invention has the beneficial effects as follows: preparation method of the present invention for raw material, is obtained by reacting Schiff compounds with aromatic amine compounds with amphene aldehyde, introduces amphene group in Schiff, finally obtain the aromatic amine Schiff containing amphene base, experimental procedure is easy, and reaction conditions is gentle, and the time is short, productive rate is high, safety and environmental protection, convenient post-treatment, secondary pollution is little.
Embodiment
Below in conjunction with the embodiment of the present invention, be clearly and completely described the technical scheme in the embodiment of the present invention, obviously, described embodiment is only the present invention's part embodiment, instead of whole embodiments.Based on the embodiment in the present invention, those of ordinary skill in the art, not making the every other embodiment obtained under creative work prerequisite, belong to the scope of protection of the invention.
A synthetic method containing amphene base Schiff compounds, it is characterized in that, concrete synthesis step is as follows:
(1) with amphene aldehyde for raw material, aromatic amine compounds is added in the reaction unit of water trap, aromatic amine is aniline or substituted aniline, and substituted aniline is the one in Ortho Toluidine, para-totuidine, para-bromoaniline, Ortho-Chloro aniline, p-Chlorobenzoic acid amide, P-nethoxyaniline, m-nitraniline, p-Nitroaniline;
Amphene aldehyde and aromatic amine are 1: 1 ~ 1.1 to feed intake in molar ratio, then add organic solvent-benzene or hexanaphthene, stirring and refluxing 2 ~ 3h, and gas phase follows the tracks of extent of reaction till target product content no longer increases;
(2) benzene in above-mentioned reaction solution or cyclohexane solvent are steamed, the thick product methyl alcohol obtained or ethanol carry out purifying, then carry out drying, and obtain amphene base Schiff compounds, its reaction formula is:
Wherein, R is the substituting group of different positions on phenyl ring.
Embodiment 1: method is led in the synthesis containing amphene base Schiff compounds (aniline and p-Chlorobenzoic acid amide)
(1) in the 150ml Erlenmeyer flask that water trap is housed, add the amphene aldehyde of 0.05mol, the p-Chlorobenzoic acid amide of 0.055mol and the hexanaphthene of 30ml, azeotropic agent is filled it up with in water trap, after stirring and refluxing 2h, follow the tracks of reaction process by gas phase, until product assay no longer increases;
(2) steamed by the hexanaphthene in reactant, underpressure distillation goes out target product amphene aldehyde anil Schiff and amphene aldehyde contracting Ortho Toluidine Schiff.
Product is as follows:
1. amphene aldehyde anil Schiff, molecular formula: C
17h
21n, molecular weight: 239.17, brown liquid, b.p.=165 ~ 167 DEG C/200Pa, purity is 95.65%, and productive rate is 73%, and the ownership of structural analysis spectral data is as follows:
FT-IR, ν
max(cm
-1): 2961,2919,2868 (C-H), 1648 (C=N), 1602,1586,1484 (phenyl ring skeletons), 763,694 (one replaces C-H)
EI-MSm/z(RA％)：77(100)，239(M
+，25.7)，240(M
++1，4.4)
1HNMR,δ
H：8.337(1H，d，J＝9.6Hz，
11-CH)，7.343(2H，t，J
1＝J
2＝7.6Hz，2
γ-CH)，7.170(1H，t，J
1＝J
2＝7.2Hz，
δ-CH)，7.132(2H，d，J＝7.6Hz，2
β-CH)，6.021(1H，d，J＝9.6Hz，
10-CH)，3.400(1H，d，J＝4.4Hz，
4-CH)，2.003(1H，d，J＝2.4Hz，
1-CH)，1.812～1.675(3H，m，
5-CH
2，
6-CH)，1.512～1.428(1H，m，
7-CH)，1.368(1H，d，J＝10Hz，
6-CH)，1.307(1H，m，
7-CH)，1.135(3H，s，
8-CH
3)，1.1027(3H，s，
9-CH
3)
13CNMR,δ
C：47.299(C
-1)，175.451(C
-2)，43.768(C
-3)，42.391(C
-4)，23.699(C
-5)，28.229(C
-6)，37.629(C
-7)，28.477(C
-8)，25.375(C
-9)，117.204(C
-10)，159.917(C
-11)，152.523(C
-α)，129.088(C
-β)，120.923(C
-γ)，125.448(C
-δ)
2. amphene aldehyde contracting Ortho Toluidine Schiff, molecular formula: C
18h
23n, molecular weight: 253.18, brown liquid, b.p.=173 ~ 175 DEG C/200Pa, purity is 98.09%, and productive rate is 69%, and the ownership of structural analysis spectral data is as follows:
FT-IR, ν
max(cm
-1): 2960,2918,2867 (C-H), 1648 (C=N), 1605,1589,1485 (phenyl ring skeletons), 754 (ortho position two replaces C-H)
EI-MSm/z(RA％)：91(100)，253(M
+，27.5)，254(M
++1，5.5)
1HNMR,δ
H：8.208(1H，d，J＝9.6Hz，
11-CH)，7.157(2H，t，J
1＝J
2＝7.2Hz，
γ’,δ-CH)，7.057(1H，d，J＝7.6Hz，
δ-CH)，6.812(1H，d，J＝7.2Hz，
β’-CH)，6.075(1H，d，J＝9.6Hz，
10-CH)，3.382(1H，d，J＝4.4Hz，
4-CH)，2.308(3H，s，
β-C-CH
3)，1.993(1H，d，J＝2.8Hz，
1-CH)，1.807～1.676(3H，m，
5-CH
2，
6-CH)，1.494～1.397(1H，m，
7-CH)，1.356(1H，d，J＝10Hz，
6-CH)，1.323～1.251(1H，m，
7-CH)，1.142(3H，s，
8-CH)，1.113(3H，s，
9-CH
3)
13CNMR,δ
C：47.359(C
-1)，174.559(C
-2)，43.742(C
-3)，42.331(C
-4)，23.728(C
-5)，28.457(C
-6)，37.637(C
-7)，28.495(C
-8)，25.428(C
-9)，117.291(C
-10)，159.626(C
-11)，152.150(C
-α)，131.441(C
-β)，125.066(C
-γ)，126.656(C
-δ)，130.171(C
-β’)，118.261(C
-γ’)，18.001(
δC–CH
3)
Embodiment 2: method is led in the synthesis containing amphene base Schiff compounds (Ortho Toluidine, para-totuidine, para-bromoaniline, Ortho-Chloro aniline, P-nethoxyaniline, m-nitraniline, p-Nitroaniline)
(1) in the 150ml Erlenmeyer flask that water trap is housed, add the amphene aldehyde of 0.05mol, the aromatic amine of 0.055mol and the hexanaphthene of 30ml, azeotropic agent is filled it up with in water trap, after stirring and refluxing 2h, follow the tracks of reaction process by gas phase, until product assay no longer increases;
(2) hexanaphthene in reactant is steamed, add ethanol, place and allow its spontaneous nucleation, after filtering out crystal, then recrystallization in ethanol, decompress filter, with cold ether drip washing solid, vacuum-drying, obtain solid powdery amphene aldehyde contracting substituted aniline Schiff.
Product is as follows:
1. amphene aldehyde contracting para-totuidine Schiff, molecular formula: C
18h
23n, molecular weight: 253.18, dark brown solid, m.p.=52.3 ~ 54.0 DEG C, purity is 96.75%, and productive rate is 86%, and the ownership of structural analysis spectral data is as follows:
FT-IR, ν
max(cm
-1): 2950,2923,2866 (C-H), 1653 (C=N), 1591,1501 (phenyl ring skeletons), 820 (contraposition two replaces C-H)
EI-MSm/z(RA％)：91(100)，253(M
+，29.9)，254(M
++1，5.2)
1HNMR,δ
H：8.351(1H，d，J＝9.6Hz，
11-CH)，6.094(1H，d，J＝9.6Hz，
10-CH)，3.403(1H，s，
4-CH)，2.337(3H，s，
δ-CH)，2.001(1H，m，
1-CH)，1.814～1677(3H，m，
5-CH
2，
6-CH)，1.467(1H，m，
7-CH)，1.368(1H，d，J＝10Hz，
6-CH)，1.271(1H，m，
7-CH)，1.128(3H，s，
8-CH)，1.100(3H，s，
9-CH
3)，7.147(2H，d，J＝8Hz，2
β-CH)，7.065(2H，d，J＝8Hz，2
γ-CH)
13CNMR,δ
C：47.231(C
-1)，175.722(C
-2)，43.750(C
-3)，42.356(C
-4)，23.592(C
-5)，28.313(C
-6)，37.540(C
-7)，28.318(C
-8)，25.243(C
-9)，116.945(C
-10)，158.949(C
-11)，149.211(C
-α)，129.639(C
-β)，120.675(C
-γ)，135.320(C
-δ)，20.896(
δC
–CH
3)
2. the contracting of amphene aldehyde is to bromo-amine Schiff, molecular formula: C
17h
20nBr, molecular weight: 317.08, light tan solid, m.p.=42.1 ~ 43.1 DEG C, purity is 97.36%, and productive rate is 76%, and the ownership of structural analysis spectral data is as follows:
FT-IR, ν
max(cm
-1): 2977,2965,2882 (C-H), 1648 (C=N), 1600,1578,1481 (phenyl ring skeletons), 835 (contraposition two replaces C-H)
EI-MSm/z(RA％)：91(100)，317(M
+，10.9)，319(M
++2，13.8)
1HNMR,δ
H：8.304(1H，d，J＝9.6Hz，
11-CH)，7.438(2H，d，J＝8.8Hz，2
γ-CH)，6.993(2H，d，J＝8.4Hz，2
β-CH)，6.036(1H，d，J＝9.6Hz，
10-CH)，3.396(1H，d，J＝4.4Hz，
4-CH)，2.007(1H，d，J＝2Hz，
1-CH)，1.824～1.673(3H，m，
5-CH
2，
6-CH)，1.518～1.419(1H，m，
7-CH)，1.376(1H，d，J＝10Hz，
6-CH)，1.303～1.1233(1H，m，
7-CH)，1.130(3H，s，
8-CH
3)，1.102(3H，s，
9-CH
3)
13CNMR,δ
C：47.251(C
-1)，176.311(C
-2)，43.830(C
-3)，42.445(C
-4)，23.671(C
-5)，28.212(C
-6)，37.624(C
-7)，28.390(C
-8)，25.320(C
-9)，117.072(C
-10)，160.101(C
-11)，151.455(C
-α)，132.070(C
-β)，122.622(C
-γ)，118.690(C
-δ)
3. amphene aldehyde contracting Ortho-Chloro aniline Schiff, molecular formula: C
17h
20nCl, molecular weight: 273.13, yellow needle-like crystals, m.p.=89.1 ~ 90.7 DEG C, purity is 96.38%, and productive rate is 87%, and the ownership of structural analysis spectral data is as follows:
FT-IR, ν
max(cm
-1): 2970,2959,2870 (C-H), 1654 (C=N), 1605,1582 (phenyl ring skeletons), 758 (ortho position two replaces C-H)
EI-MSm/z(RA％)：91(100)，273(M
+，32.0)，274(M
++1，4.3)
1HNMR,δ
H：8.262(1H，d，J＝9.6Hz，
11-CH)，7.406(1H，d，J＝1.2Hz，
γ-CH)，7.233(1H，m，
δ-CH)，7.089(1H，m，
γ’-CH)，6.938(1H，d，J＝1.2Hz，
β’-CH)，6.148(1H，d，J＝9.6Hz，
10-CH)，3.396(1H，d，J＝4.4Hz，
4-CH)，2.015(1H，d，J＝2.8Hz，
1-CH)，1.821～1.685(3H，m，
5-CH
2，
6-CH)，1.523～1.439(1H，m，
7-CH)，1.380(1H，d，J＝10.4Hz，
6-CH)，1.323～1.251(1H，m，
7-CH)，1.148(3H，s，
8-CH
3)，1.119(3H，s，
9-CH
3)
13CNMR,δ
C：47.240(C
-1)，178.674(C
-2)，43.902(C
-3)，42.389(C
-4)，23.635(C
-5)，28.172(C
-6)，37.594(C
-7)，28.359(C
-8)，25.307(C
-9)，117.134(C
-10)，161.509(C
-11)，150.080(C
-α)，127.843(C
-β)，125.866(C
-γ)，127.500(C
-δ)，129.774(C
-β’)，120.310(C
-γ’)
4. amphene aldehyde contracting p-Chlorobenzoic acid amide Schiff, molecular formula: C
17h
20nCl, molecular weight: 273.13, chocolate brown powder solid, m.p.=78.1 ~ 80.0 DEG C, purity is 95.88%, and productive rate is 78%, and the ownership of structural analysis spectral data is as follows:
FT-IR, ν
max(cm
-1): 2972,2958,2864 (C-H), 1649 (C=N), 1601,1582,1483 (phenyl ring skeletons), 857 (contraposition two replaces C-H)
EI-MSm/z(RA％)：91(100)，273(M
+，30.1)，274(M
++1，1.5)
1HNMR,δ
H：8.320(1H，d，J＝9.6Hz，
11-CH)，6.083(1H，d，J＝9.6Hz，
10-CH)，3.411(1H，s，
4-CH)，2.019(1H，s，
1-CH)，1.835～1.684(3H，m，
5-CH
2，
6-CH)，1.482(1H，m，
7-CH)，1.386(1H，d，J＝10Hz，
6-CH)，1.284(1H，m，
7-CH)，1.134(3H，s，
8-CH
3)，1.105(3H，s，
9-CH
3)，7.298(2H，d，J＝8.4Hz，2
β-CH)，7.078(2H，d，J＝8.4Hz，2
γ-CH)
13CNMR,δ
C：47.205(C
-1)，177.136(C
-2)，43.883(C
-3)，42.460(C
-4)，23.578(C
-5)，28.168(C
-6)，37.562(C
-7)，28.278(C
-8)，25.211(C
-9)，116.749(C
-10)，159.945(C
-11)，150.275(C
-α)，129.101(C
-β)，122.112(C
-γ)，130.983(C
-δ)
5. the contracting of amphene aldehyde is to methyl oxyaniline Schiff, molecular formula: C
18h
23nO, molecular weight: 269.18, grey powder solid, m.p.=61.3 ~ 62.2 DEG C, purity is 98.82%, and productive rate is 89%, and the ownership of structural analysis spectral data is as follows:
FT-IR, ν
max(cm-1): 2947,2922,2864 (C-H), 1660 (C=N), 1589,1500 (phenyl ring skeletons), 810 (contraposition two replaces)
EI-MSm/z(RA％)：77(100)，269(M
+，49.1)，270(M
++1，7.4)
1HNMR,δ
H：8.363(1H，d，J＝9.6Hz，
11-CH)，6.055(1H，d，J＝9.6Hz，
10-CH)，3.80(3H，s，OCH
3)，3.413(1H，s，
4-CH)，2.006(1H，s，
1-CH)，1.800～1.750(2H，m，
5-CH
2)，1.719～1.690(1H，m，
5-CH
2，
6-CH)，1.515～1.433(1H，m，
7-CH)，1.372(1H，d，J＝9.6Hz，
6-CH)，1.312～1.267(1H，m，
7-CH)，1.173(3H，s，
8-CH
3)，1.108(3H，s，
9-CH
3)，7.136(2H，d，J＝8.8Hz，2
γ-CH)，6.890(2H，d，J＝8.4Hz，2
β-CH)
13CNMR,δ
C：47.23(C
-1)，174.20(C
-2)，43.58(C
-3)，42.25(C
-4)，23.56(C
-5)，28.14(C
-6)，37.51(C
-7)，28.35(C
-8)，25.26(C
-9)，117.16(C
-10)，157.87(C
-11)，157.25(C
-α)，121.89(C
-β)，114.22(C
-γ)，145.30(C
-δ)，55.35(
δC
-OCH
3)
6. amphene aldehyde contracting m-nitraniline Schiff, molecular formula: C
17h
20n
2o
2, molecular weight: 284.15, yellow-brown solid, m.p.=84.6 ~ 86.6 DEG C, purity is 93.51%, and productive rate is 85%, and the ownership of structural analysis spectral data is as follows:
FT-IR, ν
max(cm
-1): 2964,2929,2870 (C-H), 1649 (C=N), 1589,1525 (phenyl ring skeletons), 1350 (NO
2), 806,739 (position two replaces C-H)
EI-MSm/z(RA％)：91(100)，284(M
+，25.7)，285(M
++1，2.0)
1HNMR,δ
H：8.378(1H，d，J＝9.6Hz，
11-CH)，6.073(1H，d，J＝9.6Hz，
10-CH)，3.455(1H，s，
4-CH)，2.041(1H，s，
1-CH)，1.871～1.704(3H，m，
5-CH
2，
6-CH)，1.505(1H，m，
7-CH)，1.419(1H，d，J＝9.6Hz，
6-CH)，1.302(1H，m，
7-CH)，1.156(3H，s，
8-CH
3)，1.128(3H，s，
9-CH
3)，8.020(1H，d，J＝7.2Hz，
δ-CH
3)，7.929(1H，s，
β-CH)，7.503(1H，t，J
1＝J
2＝8Hz，
γ’-CH)，7.435(1H，d，J＝3.6Hz，
β’-CH)
13CNMR,δ
C：47.139(C
-1)，178.220(C
-2)，43.892(C
-3)，42.482(C
-4)，23.531(C
-5)，28.138(C
-6)，37.533(C
-7)，28.226(C
-8)，25.155(C
-9)，116.705(C
-10)，161.677(C
-11)，148.793(C
-α)，129.669(C
-β)，153.606(C
-γ)，115.009(C
-δ)，127.795(C
-β’)，119.775(C
-γ’)
7. amphene aldehyde contracting p-Nitroaniline Schiff, molecular formula: C
17h
20n
2o
2, molecular weight: 284.15, chromium yellow needle-like crystals, m.p.=139.7 ~ 140.8 DEG C, purity is 99.5%, and productive rate is 89%, and the ownership of structural analysis spectral data is as follows:
FT-IR, ν
max(cm-1): 2980,2966,2885 (C-H), 1640 (C=N), 1598,1481,1445 (phenyl ring skeletons), 1505,1327 (NO
2), 900 (contraposition two replaces C-H)
EI-MSm/z(RA％)：91(100)，284(M
+，21.7)，285(M
++1，1.0)
1HNMR,δ
H：8.291(1H，d，J＝9.6Hz，
11-CH)，6.043(1H，d，J＝9.6Hz，
10-CH)，3.41(1H，s，
4-CH)，2.011(1H，s，
1-CH)，1.836～1.787(2H，m，
5-CH
2)，1.699～1.668(1H，m，
6-CH)，1.504～1.462(1H，m，
7-CH)，1.385(1H，d，J＝10Hz，
6-CH)，1.274～1.242(1H，m，
7-CH)，1.123(3H，s，
8-CH
3)，1.095(3H，s，
9-CH
3)，8.19(2H，d，J＝12.4Hz，2
γ-CH)，7.13(2H，d，J＝8.8Hz，2
β-CH)
13CNMR,δ
C：47.179(C
-1)，186.087(C
-2)，45.022(C
-3)，43.352(C
-4)，23.439(C
-5)，28.337(C
-6)，37.710(C
-7)，28.166(C
-8)，24.906(C
-9)，113.238(C
-10)，162.169(C
-11)，145.676(C
-α)，126.257(C
-β)，121.378(C
-γ)，154.389(C
-δ)。
To those skilled in the art, obviously the invention is not restricted to the details of above-mentioned one exemplary embodiment, and when not deviating from spirit of the present invention or essential characteristic, the present invention can be realized in other specific forms.Therefore, no matter from which point, all should embodiment be regarded as exemplary, and be nonrestrictive, scope of the present invention is limited by claims instead of above-mentioned explanation, and all changes be therefore intended in the implication of the equivalency by dropping on claim and scope are included in the present invention.
Claims (6)
1. the synthetic method containing amphene base Schiff compounds, it is characterized in that, concrete synthesis step is as follows:
(1) with amphene aldehyde for raw material, aromatic amine compounds is added at the reaction unit of organic solvent, amphene aldehyde and aromatic amine are 1: 1 ~ 1.1 to feed intake in molar ratio, stirring and refluxing 2 ~ 3h, and gas phase follows the tracks of extent of reaction till target product content no longer increases;
(2) benzene in above-mentioned reaction solution or cyclohexane solvent are steamed, the thick product solvent obtained carries out purifying, then carries out drying, and obtain amphene base Schiff compounds, its reaction formula is:
Wherein, R is the substituting group of different positions on phenyl ring.
2. the synthetic method containing amphene base Schiff compounds according to claim 1, it is characterized in that, described aromatic amine includes but not limited to aniline or substituted aniline.
3. the synthetic method containing amphene base Schiff compounds according to claim 2, it is characterized in that, described substituted aniline includes but not limited to Ortho Toluidine, para-totuidine, para-bromoaniline, Ortho-Chloro aniline, p-Chlorobenzoic acid amide, P-nethoxyaniline, m-nitraniline, p-Nitroaniline.
4. the synthetic method containing amphene base Schiff compounds according to claim 1, it is characterized in that, described organic solvent is benzene or cyclohexane.
5. the synthetic method containing amphene base Schiff compounds according to claim 1, it is characterized in that, described reaction unit is the reaction unit with water trap.
6. the synthetic method containing amphene base Schiff compounds according to claim 1, it is characterized in that, solvent that this purifying uses is methyl alcohol or ethanol.
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| CN106083633A (en) * | 2016-06-12 | 2016-11-09 | 江西农业大学 | A kind of synthetic method of isocamphanyl Carbox amide |
| CN113880786A (en) * | 2021-10-16 | 2022-01-04 | 江西农业大学 | Synthesis method and antioxidant application of camphene aldehyde thiazole hydrazone derivative |
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| CN106083633A (en) * | 2016-06-12 | 2016-11-09 | 江西农业大学 | A kind of synthetic method of isocamphanyl Carbox amide |
| CN106083633B (en) * | 2016-06-12 | 2021-08-24 | 江西农业大学 | Synthetic method of isoborneol formamide compound |
| CN113880786A (en) * | 2021-10-16 | 2022-01-04 | 江西农业大学 | Synthesis method and antioxidant application of camphene aldehyde thiazole hydrazone derivative |
| CN113880786B (en) * | 2021-10-16 | 2023-03-03 | 江西农业大学 | Synthesis method and anti-oxidation application of camphene aldehyde thiazole hydrazone derivative |
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