CN106749346A - A kind of new method for preparing adjacent dinitro dibenzyl - Google Patents
A kind of new method for preparing adjacent dinitro dibenzyl Download PDFInfo
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- CN106749346A CN106749346A CN201611191486.7A CN201611191486A CN106749346A CN 106749346 A CN106749346 A CN 106749346A CN 201611191486 A CN201611191486 A CN 201611191486A CN 106749346 A CN106749346 A CN 106749346A
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- dibenzyl
- dinitro
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- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- 238000003756 stirring Methods 0.000 claims description 24
- -1 nitro bromobenzene grignard reagent Chemical class 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 14
- 239000011777 magnesium Substances 0.000 claims description 14
- 229910052749 magnesium Inorganic materials 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000012043 crude product Substances 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 230000000977 initiatory effect Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000005498 polishing Methods 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- 238000007789 sealing Methods 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- FBLDLJMRGSZGCD-UHFFFAOYSA-N 2-(2-nitrophenyl)ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC1=CC=CC=C1[N+]([O-])=O FBLDLJMRGSZGCD-UHFFFAOYSA-N 0.000 claims description 3
- 239000002994 raw material Substances 0.000 abstract description 8
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 abstract description 4
- 229960000623 carbamazepine Drugs 0.000 abstract description 4
- 150000004795 grignard reagents Chemical class 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003556 anti-epileptic effect Effects 0.000 abstract description 3
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000001228 spectrum Methods 0.000 abstract description 3
- 230000035800 maturation Effects 0.000 abstract description 2
- DSDBYQDNNWCLHL-UHFFFAOYSA-N 1-(2-nitrophenyl)ethanol Chemical compound CC(O)C1=CC=CC=C1[N+]([O-])=O DSDBYQDNNWCLHL-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- KFDLHDGFDLHFRW-UHFFFAOYSA-N [O-][N+](Br)=O Chemical group [O-][N+](Br)=O KFDLHDGFDLHFRW-UHFFFAOYSA-N 0.000 description 4
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of preparation method of wide spectrum antiepileptic carbamazepine intermediate, and in particular to a kind of new method of prepare compound neighbour dinitro dibenzyl.The method is prepared into corresponding grignard reagent with nitro bromobenzene as raw material, is then reacted with protected o-nitrophenylethanol, prepares product.The present invention, as raw material, is prepared into grignard reagent using nitro bromobenzene so that reaction is more gentle, avoid and produce hydrogen in course of reaction, the security of production is greatly improved, and reaction yield and selectivity are more preferably, and the utilization rate of raw material is higher, also there is preferably improvement to the cost control of product, and raw material process maturation, ample supply of commodities on the market and wide material sources, process is simple, it is easy to operation, lossless environment.
Description
Technical field
The present invention relates to a kind of preparation method of wide spectrum antiepileptic carbamazepine intermediate, and in particular to one kind preparation
The new method of compound neighbour's dinitro dibenzyl.
Background technology
Carbamazepine (Carbamazepine) is most effective to psychomotor attack as a kind of wide spectrum antiepileptic, right
Big breaking-out, limitation breaking-out and mixed type epilepsy also effectively, mitigate insanity and the epilepsy with mental symptom are particularly fitted
Preferably.Have been widely used for the treatment of such disease at present, and such medicine use normalization, traction
Height, if improving its technique, reduces cost, the key as the similar drug further genralrlization.
And compound neighbour dinitro dibenzyl as the key intermediate for directly affecting its quality and cost, its research is also card
Focus and difficult point in the technical study of horse Xiping.The current synthesis on adjacent dinitro dibenzyl is mainly by with adjacent toluene as former
In material, kerosene or relative high boiling solvent, reacted with Ethyl formate in the presence of sodium methoxide, prepare product neighbour's dinitro
Dibenzyl, although the method have been carried out industrialization, but because it produces hydrogen during the course of the reaction, to operate requirement compared with
Height, production process has larger risk of explosion.
The application one brand-new synthetic route by a series of experimental summary, using nitro bromobenzene as original
Material, is prepared into grignard reagent so that reaction is more gentle, it is to avoid produces hydrogen in course of reaction, greatly improves production
Security, and reaction yield and selectivity more preferably, the utilization rate of raw material is higher, and the cost control to product also has preferably
Improve.
The content of the invention
It is an object of the invention to provide a kind of process is simple, the system of the adjacent dinitro dibenzyl for being easy to operation and lossless environment
Preparation Method.
It is up to above-mentioned purpose, we have proposed a brand-new synthetic route.
Realize that technical scheme is as follows：
A kind of new method for preparing adjacent dinitro dibenzyl, is obtained in accordance with the following steps with the adjacent dinitro dibenzyl that formula (I) is represented
：
Its specific preparation method is as follows：
(1) nitro bromobenzene (II), tetrahydrochysene are added in the reactor with stirring, heater and reflux condensate device
Furans and iodine, are dividedly in some parts the magnesium chips of polishing after stirring, then heat to micro-boiling, until initiation reaction, then controls to add
Hot amplitude, keeps reactant mixture slight boiling condition, until magnesium chips disappears substantially, the nitro bromobenzene grignard reagent for preparing is close
Envelope is stand-by, and the weight between nitro bromobenzene, tetrahydrofuran, iodine, magnesium chips is than control 1:5-10:0.01:0.11-0.15；
(2) tetrahydrofuran, tetrachloro is added to close copper two lithiums of acid and p-methyl benzenesulfonic acid (ortho-nitrophenyl second in another reactor
Base) ester (III), tetrahydrofuran, tetrachloro close mass ratio control between two lithiums of copper acid, p-methyl benzenesulfonic acid (ortho-nitrophenyl ethyl) ester and exist
2-3:0.5:1.58-1.59；The nitro bromobenzene form examination for adding step (1) to prepare is added dropwise after stirring at room temperature
Agent, dropping temperature is no more than 30 DEG C, 55-60 DEG C is warming up to after completion of dropping and continues stirring reaction 6-10 hours；After reaction terminates
A small amount of watery hydrochloric acid is added, insoluble matter is filtered to remove, filtrate decompression is distilled off most of solvent, the residue for obtaining is analysed after standing
Go out solid, obtain yellow powder, be adjacent dinitro dibenzyl (I) crude product, through recrystallisation from isopropanol after, obtain pale yellow powder, be
Adjacent dinitro dibenzyl (I) fine work.
Advantages of the present invention：
The present invention, as raw material, is prepared into grignard reagent using nitro bromobenzene so that reaction is more gentle, it is to avoid anti-
Hydrogen is produced during answering, the security of production is greatly improved, and reaction yield and selectivity are more preferably, the utilization of raw material
Rate is higher, also has preferably improvement, and raw material process maturation, ample supply of commodities on the market and wide material sources to the cost control of product,
Process is simple, is easy to operation, lossless environment.
Specific embodiment
Further illustrate how the present invention realizes below by specific embodiment：
Embodiment 1
Added in stirring, the reactor of heater and reflux condensate device nitro bromobenzene (II) (202g,
1.0mol), tetrahydrofuran (2000g) and iodine (2.02g), be dividedly in some parts after stirring polishing magnesium chips (28.8g,
1.2mol), micro-boiling is then heated to, until initiation reaction, then controls heating amplitude, reactant mixture slight boiling condition is kept,
Until magnesium chips disappears substantially, the nitro bromobenzene grignard reagent sealing for preparing is stand-by；
Tetrahydrofuran (600g) is added in another reactor, tetrachloro closes copper two lithiums of acid (101g) and p-methyl benzenesulfonic acid is (adjacent
Nitrophenethyl) ester (III) (321g, 1.0mol), it is added dropwise at room temperature after stirring and adds adjacent nitro bromine well prepared in advance
Benzene grignard reagent, dropping temperature is no more than 30 DEG C, 55-60 DEG C is warming up to after completion of dropping and continues stirring reaction 10 hours；Reaction
A small amount of watery hydrochloric acid is added after end, insoluble matter is filtered to remove, filtrate decompression is distilled off most of solvent, and the residue for obtaining is quiet
Postpone precipitation solid, obtain yellow powder, be adjacent dinitro dibenzyl (I) crude product, through recrystallisation from isopropanol after, obtain yellowish toner
End, is adjacent dinitro dibenzyl (I) fine work.It is 195.8g, yield about 72.0%.Fusing point：120-122.5℃.1H NMR (CDCl3,
500MHz)δ：2.79-2.83 (4H, t), 7.55-8.06 (8H, m).FAB-MS(m/z)：:273(M+H).
Embodiment 2
Added in stirring, the reactor of heater and reflux condensate device nitro bromobenzene (II) (202g,
1.0mol), tetrahydrofuran (1050g) and iodine (2.02g), are dividedly in some parts the magnesium chips (24g, 1.0mol) of polishing after stirring,
Micro-boiling is then heated to, until initiation reaction, then controls heating amplitude, reactant mixture slight boiling condition is kept, until magnesium chips
Basic to disappear, the nitro bromobenzene grignard reagent sealing for preparing is stand-by；
Tetrahydrofuran (410g) is added in another reactor, tetrachloro closes copper two lithiums of acid (101g) and p-methyl benzenesulfonic acid is (adjacent
Nitrophenethyl) ester (III) (321g, 1.0mol), it is added dropwise at room temperature after stirring and adds adjacent nitro bromine well prepared in advance
Benzene grignard reagent, dropping temperature is no more than 30 DEG C, 55-60 DEG C is warming up to after completion of dropping and continues stirring reaction 6 hours；Reaction knot
A small amount of watery hydrochloric acid is added after beam, insoluble matter is filtered to remove, filtrate decompression is distilled off most of solvent, the residue for obtaining stands
After separate out solid, obtain yellow powder, be adjacent dinitro dibenzyl (I) crude product, through recrystallisation from isopropanol after, obtain yellowish toner
End, is adjacent dinitro dibenzyl (I) fine work.It is 165.3g, yield about 60.8%.Fusing point：120-122.5℃.1H NMR (CDCl3,
500MHz)δ：2.79-2.83 (4H, t), 7.55-8.06 (8H, m).FAB-MS(m/z)：:273(M+H).
Embodiment 3
Added in stirring, the reactor of heater and reflux condensate device nitro bromobenzene (II) (202g,
1.0mol), tetrahydrofuran (1500g) and iodine (2.02g).Be dividedly in some parts after stirring polishing magnesium chips (26.4g,
1.1mol), micro-boiling is then heated to, until initiation reaction, then controls heating amplitude, reactant mixture slight boiling condition is kept,
Until magnesium chips disappears substantially, the nitro bromobenzene grignard reagent sealing for preparing is stand-by；
Tetrahydrofuran (500g) is added in another reactor, tetrachloro closes copper two lithiums of acid (101g) and p-methyl benzenesulfonic acid is (adjacent
Nitrophenethyl) ester (III) (321g, 1.0mol), it is added dropwise at room temperature after stirring and adds adjacent nitro bromine well prepared in advance
Benzene grignard reagent, dropping temperature is no more than 30 DEG C, 55-60 DEG C is warming up to after completion of dropping and continues stirring reaction 8 hours；Reaction knot
A small amount of watery hydrochloric acid is added after beam, insoluble matter is filtered to remove, filtrate decompression is distilled off most of solvent, the residue for obtaining stands
After separate out solid, obtain yellow powder, be adjacent dinitro dibenzyl (I) crude product, through recrystallisation from isopropanol after, obtain yellowish toner
End, is adjacent dinitro dibenzyl (I) fine work.It is 173.5g, yield about 63.8%.Fusing point：120-122.5℃.1H NMR (CDCl3,
500MHz)δ：2.79-2.83 (4H, t), 7.55-8.06 (8H, m).FAB-MS(m/z)：:273(M+H).
Embodiment 4
Added in stirring, the reactor of heater and reflux condensate device nitro bromobenzene (II) (202g,
1.17mol), tetrahydrofuran (1800g) and iodine (2.02g), are dividedly in some parts the magnesium chips (28g, 1.2mol) of polishing after stirring,
Micro-boiling is then heated to, until initiation reaction, then controls heating amplitude, reactant mixture slight boiling condition is kept, until magnesium chips
Basic to disappear, the nitro bromobenzene grignard reagent sealing for preparing is stand-by；
Tetrahydrofuran (500g) is added in another reactor, tetrachloro closes copper two lithiums of acid (101g) and p-methyl benzenesulfonic acid is (adjacent
Nitrophenethyl) ester (III) (321g, 1.0mol), it is added dropwise at room temperature after stirring and adds adjacent nitro bromine well prepared in advance
Benzene grignard reagent, dropping temperature is no more than 30 DEG C, 55-60 DEG C is warming up to after completion of dropping and continues stirring reaction 9 hours；Reaction knot
A small amount of watery hydrochloric acid is added after beam, insoluble matter is filtered to remove, filtrate decompression is distilled off most of solvent, the residue for obtaining stands
After separate out solid, obtain yellow powder, be adjacent dinitro dibenzyl (I) crude product, through recrystallisation from isopropanol after, obtain yellowish toner
End, is adjacent dinitro dibenzyl (I) fine work.It is 181.9g, yield about 66.9%.Fusing point：120-122.5℃.1H NMR (CDCl3,
500MHz)δ：2.79-2.83 (4H, t), 7.55-8.06 (8H, m).FAB-MS(m/z)：:273(M+H).Although inventor is
More detailed elaboration is done to technical scheme and has been enumerated, it will be appreciated that for the masterful technique of this area one
For personnel, above-described embodiment is modified and/or flexible or be obvious using equivalent alternative solution, can not all taken off
The term occurred in the essence of spirit of the present invention, the present invention is used for elaboration and understanding to technical solution of the present invention, can not
It is construed as limiting the invention.
Claims (1)
1. a kind of new method for preparing adjacent dinitro dibenzyl, it is characterised in that：The adjacent dinitro dibenzyl represented with formula (I) is according to such as
Lower step is obtained：
Its specific preparation method is as follows：
(1) nitro bromobenzene (II), tetrahydrofuran are added in the reactor with stirring, heater and reflux condensate device
And iodine, the magnesium chips of polishing is dividedly in some parts after stirring, micro-boiling is then heated to, until initiation reaction, then controls heating width
Degree, keeps reactant mixture slight boiling condition, until magnesium chips disappears substantially, the nitro bromobenzene grignard reagent sealing for preparing is treated
With the weight between nitro bromobenzene, tetrahydrofuran, iodine, magnesium chips is than control 1:5-10:0.01:0.11-0.15；
(2) tetrahydrofuran, tetrachloro is added to close copper two lithiums of acid and p-methyl benzenesulfonic acid (ortho-nitrophenyl ethyl) ester in another reactor
(III), tetrahydrofuran, tetrachloro close mass ratio between two lithiums of copper acid, p-methyl benzenesulfonic acid (ortho-nitrophenyl ethyl) ester and control in 2-3:
0.5:1.58-1.59；The nitro bromobenzene grignard reagent for adding step (1) to prepare, drop is added dropwise after stirring at room temperature
Heating degree is no more than 30 DEG C, 55-60 DEG C is warming up to after completion of dropping and continues stirring reaction 6-10 hours；Reaction adds few after terminating
Amount watery hydrochloric acid, is filtered to remove insoluble matter, and filtrate decompression is distilled off most of solvent, and the residue for obtaining separates out solid after standing
Body, obtains yellow powder, is adjacent dinitro dibenzyl (I) crude product, through recrystallisation from isopropanol after, obtain pale yellow powder, be adjacent two
Nitro dibenzyl (I) fine work.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109053453A (en) * | 2018-08-29 | 2018-12-21 | 江苏师范大学 | A kind of synthetic method of α-o-nitrophenylethanol |
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2016
- 2016-12-21 CN CN201611191486.7A patent/CN106749346A/en active Pending
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| CN101298496A (en) * | 2008-07-01 | 2008-11-05 | 电子科技大学 | Conductive polymers hydrogen bond acidic air-sensitive material |
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| CN104628555A (en) * | 2015-01-05 | 2015-05-20 | 烟台蓓丰医药科技有限公司 | Synthesis method of drug intermediate 4-(4-chlorphenyl) cyclohexyl-1-formic acid |
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Application publication date: 20170531 |