CN106565517A - Method for preparing amide from aryl methane derivative and nitrile - Google Patents
Method for preparing amide from aryl methane derivative and nitrile Download PDFInfo
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- CN106565517A CN106565517A CN201610905548.XA CN201610905548A CN106565517A CN 106565517 A CN106565517 A CN 106565517A CN 201610905548 A CN201610905548 A CN 201610905548A CN 106565517 A CN106565517 A CN 106565517A
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- Prior art keywords
- nitrile
- derivant
- arylmethane
- amide
- prepared
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- -1 aryl methane derivative Chemical class 0.000 title claims abstract description 34
- 150000002825 nitriles Chemical class 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 29
- 150000001408 amides Chemical class 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000007800 oxidant agent Substances 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 52
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- KTOXGWMDJYFBKK-UHFFFAOYSA-L manganese(2+);diacetate;dihydrate Chemical compound O.O.[Mn+2].CC([O-])=O.CC([O-])=O KTOXGWMDJYFBKK-UHFFFAOYSA-L 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 23
- 238000005292 vacuum distillation Methods 0.000 claims description 23
- 239000012043 crude product Substances 0.000 claims description 22
- 239000012467 final product Substances 0.000 claims description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 20
- 241001597008 Nomeidae Species 0.000 claims description 19
- 125000006840 diphenylmethane group Chemical group 0.000 claims description 9
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000011572 manganese Substances 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 4
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 4
- PQTAUFTUHHRKSS-UHFFFAOYSA-N 1-benzyl-2-methylbenzene Chemical compound CC1=CC=CC=C1CC1=CC=CC=C1 PQTAUFTUHHRKSS-UHFFFAOYSA-N 0.000 claims description 3
- KSYQGOYOIKQFNA-UHFFFAOYSA-N 1-benzyl-3-methylbenzene Chemical compound CC1=CC=CC(CC=2C=CC=CC=2)=C1 KSYQGOYOIKQFNA-UHFFFAOYSA-N 0.000 claims description 3
- ADCBAIUWZPOIMC-UHFFFAOYSA-N 1-benzyl-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1CC1=CC=CC=C1 ADCBAIUWZPOIMC-UHFFFAOYSA-N 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 229940071125 manganese acetate Drugs 0.000 claims description 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 claims description 2
- 230000004044 response Effects 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical group OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 claims description 2
- 229940005561 1,4-benzoquinone Drugs 0.000 claims 1
- GQLYCRTUQGSDSM-UHFFFAOYSA-N 1-benzyl-4-methoxybenzene Chemical class C1=CC(OC)=CC=C1CC1=CC=CC=C1 GQLYCRTUQGSDSM-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 abstract description 36
- 239000002994 raw material Substances 0.000 abstract description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 abstract description 3
- 239000011737 fluorine Substances 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 abstract 4
- ONJSLAKTVIZUQS-UHFFFAOYSA-K manganese(3+);triacetate;dihydrate Chemical compound O.O.[Mn+3].CC([O-])=O.CC([O-])=O.CC([O-])=O ONJSLAKTVIZUQS-UHFFFAOYSA-K 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 description 48
- 230000015572 biosynthetic process Effects 0.000 description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
- 239000000047 product Substances 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- 238000003810 ethyl acetate extraction Methods 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 238000000926 separation method Methods 0.000 description 20
- 238000002156 mixing Methods 0.000 description 19
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 16
- 238000010189 synthetic method Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 3
- NPOGRKGIBGKRNI-UHFFFAOYSA-N 1-benzyl-4-chlorobenzene Chemical class C1=CC(Cl)=CC=C1CC1=CC=CC=C1 NPOGRKGIBGKRNI-UHFFFAOYSA-N 0.000 description 2
- SIYISNUJKMAQBV-UHFFFAOYSA-N 1-benzyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1CC1=CC=CC=C1 SIYISNUJKMAQBV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- MTXCBBSDWXDJKB-UHFFFAOYSA-N n-[(2-methylphenyl)-phenylmethyl]acetamide Chemical compound C=1C=CC=C(C)C=1C(NC(=O)C)C1=CC=CC=C1 MTXCBBSDWXDJKB-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 108010046334 Urease Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- QNEFNFIKZWUAEQ-UHFFFAOYSA-N carbonic acid;potassium Chemical compound [K].OC(O)=O QNEFNFIKZWUAEQ-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- ZICQBHNGXDOVJF-UHFFFAOYSA-N diamantane Chemical compound C1C2C3CC(C4)CC2C2C4C3CC1C2 ZICQBHNGXDOVJF-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 150000002468 indanes Chemical class 0.000 description 1
- JWWVWJOIKZNCSU-UHFFFAOYSA-N methanesulfonic acid;2,2,2-trifluoroacetic acid Chemical class CS(O)(=O)=O.OC(=O)C(F)(F)F JWWVWJOIKZNCSU-UHFFFAOYSA-N 0.000 description 1
- ITEUFGALZZEACE-UHFFFAOYSA-N n-[(4-methylphenyl)-phenylmethyl]acetamide Chemical compound C=1C=C(C)C=CC=1C(NC(=O)C)C1=CC=CC=C1 ITEUFGALZZEACE-UHFFFAOYSA-N 0.000 description 1
- ZDHMLHRXLMDODX-UHFFFAOYSA-N n-benzhydryl-2-methylpropanamide Chemical class C=1C=CC=CC=1C(NC(=O)C(C)C)C1=CC=CC=C1 ZDHMLHRXLMDODX-UHFFFAOYSA-N 0.000 description 1
- FNOLFYLSHDEZII-UHFFFAOYSA-N n-benzhydryl-2-phenylacetamide Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)NC(=O)CC1=CC=CC=C1 FNOLFYLSHDEZII-UHFFFAOYSA-N 0.000 description 1
- WEASGADRJWKQRE-UHFFFAOYSA-N n-benzhydrylacetamide Chemical class C=1C=CC=CC=1C(NC(=O)C)C1=CC=CC=C1 WEASGADRJWKQRE-UHFFFAOYSA-N 0.000 description 1
- NAMNSMRPXCPPFE-UHFFFAOYSA-N n-benzhydrylbenzamide Chemical class C=1C=CC=CC=1C(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 NAMNSMRPXCPPFE-UHFFFAOYSA-N 0.000 description 1
- UNPWIWFUSOEVKO-UHFFFAOYSA-N n-benzhydrylpentanamide Chemical class C=1C=CC=CC=1C(NC(=O)CCCC)C1=CC=CC=C1 UNPWIWFUSOEVKO-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention provides a simple and efficient method for directly preparing an amide compound from an aryl methane derivative and nitrile. In the method, manganese triacetate dihydrate is used as a catalyst, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) is used as an oxidizing agent. The method has the characteristics that raw materials are cheap and easy to obtain, the source of the nitrile is wide, reaction conditions are mild, the applicability is wide and the like. The method solves the problems that ceric ammonium nitrate (CAN) and a fluorine agent which are used by a method for directly synthesizing amide by using aryl methane and nitrile compounds are hard to treat, atomic economy is poor, the source of the nitrile is narrow and the like.
Description
【Technical field】
The present invention relates to organic synthesis field, and in particular to a kind of side that amide is prepared by arylmethane derivant and nitrile
Method.
【Background technology】
Amides compound is important organic synthesiss raw material and intermediate, has been attracted very in industry and sphere of learning in recent years
The interest of many people.Peptide bond can be formed in the protein such as enzyme, in terms of biological, pesticide higher value is shown, and
And also show good biological medicinal activity in field of medicaments.Not only there is amides compound excellent biological activity also to have
Changeable chemical constitution, is one of focus that organic synthesiss are studied with pharmaceutical chemistry, with regard to the spy of this kind of compound synthesis route
Rope is also constantly deeply.
Carboxylic acid or acid chloride or anhydrides compound generate amides compound with amine reaction, are using wider synthesis side
Method.Also someone synthesizes primary amine with aldehyde compound and azanol.Metal cyanides are using cyanylation agent earlier.It is this
The shortcoming of method is：With poisonous or hygroscopic catalyst, and costly metal trifluoroacetate methanesulfonates is also needed to, be not inconsistent combination
Work produces the requirement of environmental protection.In the last few years, increasing nitrile was utilized.2011, Kalkhambkar problems
Group, it was recently reported that with diamantane (obsolete) as substrate, nitrile compounds are nitrile source, mix catalyst, have synthesized required amides compound.
2013, Panduranga etc. was reported with ether compound as substrate, and cyanamide is nitrile source, you can obtain dibasic urease
Product.
At present the method for being directly synthesized amide by arylmethane and nitrile compounds of report has five kinds, but these method nitriles
Source is narrower and nitrile is used as solvent, and using the oxidant being of little use, such as ammonium ceric nitrate (CAN) and fluorine reagent etc. are more intractable
And Atom economy is bad, they are much higher for similar compound our productivity ratio.Therefore new mild condition, substrate is suitable for
Property it is wide, high selectivity, the method for the synthesizing amide class compound of high atom economy is constantly subjected to the attention of people.【With reference to text
Offer：Kalkhambkar,R.G.,Waters,S.N.,Laali,K.K.,Tetrahedron Lett.,2011,52,867–871；
Panduranga,V.,Basavaprabhu,H.,Sureshbabu,V.V.,Tetrahedron Lett.,2013,54,975–
979.Sakaguchi,S.,Hirabayashi,T.,Ishii,Y.,Chem Comm.,2002,516；Nair,V.,Suja,
T.D.,Mohanan,K.,Tetrahedron Lett.,2005,46,3217；Michaudel,Q.,Thevenet,D.,
Baran,P.S.,J Am Chem Soc.,2012,134,2547.Liu,C.,Zhang,Q.,Li,H.,Guo,S.,Xiao,B.,
Deng,W.,Liu,L.,He,W.,Chem.-Eur.J.2016,22,1.】
For the deficiency of said method, exploitation does not use reluctant oxidant, does not use part strong acid, operation letter
The synthesis new way of single, applied widely amides compound, with potential prospects for commercial application.
【The content of the invention】
The purpose of the present invention is that exploitation is a kind of under nitrogen atmosphere, using Mn catalyst, with arylmethane derivant and nitrile
Class compound is the method for raw material, high conversion and high productivity synthesizing amide class compound.The purpose of the present invention is by such as
What lower technical scheme was realized：
A kind of structural formula isAmides compound synthetic method, comprise the steps of：
Arylmethane derivant, nitrile compounds, Mn catalyst, oxidant, trifluoroacetic acid (TFA), solvent are placed in instead
In answering container, mixing under nitrogen atmosphere, at reaction temperature is for 70～90 DEG C, continues 8～16h of stirring reaction, and reaction terminates
After be cooled to room temperature, add potassium carbonate to neutrality, then extracted with organic solvent, be dried, vacuum distillation concentration removes solvent, slightly
Product Jing pillar layer separations, obtain final product amides compound.
In the structure Formulas I, R1It is aryl, fat-based, hydrogen；R2Be methyl, normal-butyl, isopropyl, the tert-butyl group, cyclopropyl,
Vinyl, benzyl, phenyl.
In above-mentioned synthetic method, described Mn catalyst is at least one in manganese acetate and acetate dihydrate manganese.
In above-mentioned synthetic method, described nitrile compounds be acetonitrile, valeronitrile, isopropyl cyanide, trimethylacetonitrile, cyclopropylniitrile,
At least one in acrylonitrile, benzonitrile, benzene acetonitrile.
In above-mentioned synthetic method, described oxidant is 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).
In above-mentioned synthetic method, the aromatic methane derivant selected from diphenyl methane, ethylbenzene, isobutyl-benzene, indane,
Fluorenes, 1,2,3,4- naphthanes, 1- benzyl -4- chlorobenzenes, double (4- fluorophenyls) methane, 1- benzyl -4- fluorobenzene, 1- benzyl -4- methyl
Benzene, 1- benzyl -3- methylbenzene, 1- benzyl -2- methylbenzene.
In above-mentioned synthetic method, additive is trifluoroacetic acid (TFA) in the course of reaction.
In above-mentioned synthetic method, solvent is in acetonitrile, 1,2- dichloroethanes (DCE) and toluene in the course of reaction
At least one, when acetonitrile solvent is, it also functions as reaction reagent.
In above-mentioned synthetic method, the Mn catalyst, DDQ oxidants, trifluoroacetic acid, nitrile compounds and arylmethane spread out
Mol ratio between biology is [0.1～0.3]：[1.0～3.0]：[15～25]：[15～50]：1, reaction temperature is 70～90
DEG C, the response time is 8～16h.
In above-mentioned synthetic method, the organic solvent in the extraction step is ethyl acetate, chloroform or dichloromethane.
According to experimental result, the invention provides one kind directly prepares amides compound by arylmethane derivant and nitrile
Simple efficient method.The method uses acetate dihydrate manganese as catalyst, 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
(DDQ) as oxidant, with raw material is cheap and easy to get, nitrile source compared with it is wide, reaction condition is gentle, the suitability is wide the features such as.The method
Solve arylmethane and nitrile compounds are directly synthesized ammonium ceric nitrate (CAN) used in the method for amide and fluorine reagent is more difficult
Process, the problems such as Atom economy is bad, nitrile source is narrower.
【Brief Description Of Drawings】
Fig. 1 is the reaction equation that amides compound is prepared by aromatic methane.
【Specific embodiment】
Synthetic method of the present invention is described further with reference to the synthesis example of the present invention, needs explanation
It is that embodiment does not constitute the restriction to the claimed scope of the invention.
As shown in figure 1, the synthesis step of the amides compound of present invention offer is：Arylmethane derivant, manganese are urged
Agent (mol ratio 10%～200% is based on aromatic methane), oxidant (mol ratio 100%～300% is based on aromatic methane), nitrile
Class compound (mol ratio 1500%～5000% is based on aromatic methane), trifluoroacetic acid and solvent are placed in reaction vessel, are mixed,
In nitrogen atmosphere, at reaction temperature is for 70～90 DEG C, continue 8～16h of stirring reaction, reaction is cooled to room temperature after terminating,
Add potassium carbonate to neutrality, then extracted with organic solvent, be dried, vacuum distillation concentration removes solvent, crude product Jing column chromatography
Separate, obtain final product amides compound.
Synthesis example 1
The synthesis of N- benzhydryl acetamides
0.2mmol diphenyl methanes, 0.04mmol acetate dihydrate manganese, 0.4mmolDDQ, 0.5mL second are added in the reactor
Nitrile, 0.15mL TFA, mixing is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to room temperature, adds carbon
Sour potassium, with ethyl acetate extraction, is dried to neutrality, and vacuum distillation removes solvent, and crude product Jing pillar layer separation obtains final product target product
Thing, yield 90%.1H NMR(400MHz,CDCl3)：δ 7.34-7.26 (m, 6H), 7.24-7.21 (m, 4H), 6.24 (d, J=
8.0Hz, 1H), 6.09 (d, J=6.2Hz, 1H), 2.06 (s, 3H).
Synthesis example 2
The synthesis of N- (1- phenethyls) acetamide
In the reactor add 0.2mmol ethylbenzene, 0.04mmol acetate dihydrate manganese, 0.4mmol DDQ, 0.5mL acetonitriles,
0.15mL TFA, mixing, are heated under a nitrogen 90 DEG C, persistently stir 12h, and stopped reaction is cooled to room temperature, adds potassium carbonate
To neutral, with ethyl acetate extraction, it is dried, vacuum distillation removes solvent, and crude product Jing pillar layer separation obtains final product target product, produces
Rate 59%.1H NMR(400MHz,CDCl3)：δ7.27-7.18(m,5H),5.83(s,1H),5.07–4.99(m,1H),1.89
(s, 3H), 1.40 (d, J=6.9Hz, 1H).
Synthesis example 3
The synthesis of N- (2- methyl isophthalic acids-phenyl propyl) acetamide
0.2mmol isobutyl-benzenes, 0.04mmol acetate dihydrate manganese, 0.4mmolDDQ, 0.5mL second are added in the reactor
Nitrile, 0.15mL TFA, mixing is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to room temperature, adds carbon
Sour potassium, with ethyl acetate extraction, is dried to neutrality, and vacuum distillation removes solvent, and crude product Jing pillar layer separation obtains final product target product
Thing, yield 20%.1H NMR(400MHz,CDCl3)：δ 7.25 (d, J=7.6Hz, 1H), 7.19-7.14 (m, 4H), 7.16 (d, J
=8.3Hz, 2H), 5.67 (d, J=7.4Hz, 1H), 4.69 (t, J=8.5Hz, 1H), 2.00-1.95 (m, 1H), 1.93 (s,
3H), 0.90 (d, J=6.7Hz, 3H), 0.76 (d, J=6.7Hz, 3H).
Synthesis example 4
The synthesis of N- (2,3- dihydro -1H- indenes -1- bases) acetamide
In the reactor add 0.2mmol indanes, 0.02mmol acetate dihydrate manganese, 0.24mmol DDQ, 0.15mL acetonitriles,
0.15mL TFA, 0.35mL DCE mixes, and 70 DEG C are heated under a nitrogen, persistently stirs 12h, and stopped reaction is cooled to room temperature,
Add potassium carbonate to neutrality, with ethyl acetate extraction, be dried, vacuum distillation removes solvent, and crude product Jing pillar layer separation is obtained final product
Target product, yield 75%.1H NMR(400MHz,CDCl3)：δ7.18-7.08(m,4H),5.99(s,1H),5.35-5.28
(m,1H),2.89-2.83(m,2H),2.49-2.41(m,1H),1.89(s,3H),1.74-1.65(m,1H)。
Synthesis example 5
The synthesis of N- (1,2,3,4- naphthane -1- bases) acetamide
In the reactor add the naphthanes of 0.2mmol 1,2,3,4-, 0.04mmol acetate dihydrate manganese, 0.4mmol DDQ,
0.5mL acetonitriles, 0.15mL TFA, mixing is heated under a nitrogen 60 DEG C, persistently stirs 12h, and stopped reaction is cooled to room temperature,
Add potassium carbonate to neutrality, with ethyl acetate extraction, be dried, vacuum distillation removes solvent, and crude product Jing pillar layer separation is obtained final product
Target product, yield 57%.1H NMR(400MHz,CDCl3)：δ7.25-7.06(m,4H),5.92(s,1H),5.15-5.12
(m,1H),2.81-2.69(m,2H),2.02-1.99(m,1H),1.97(s,3H),1.84-1.77(m,3H)。
Synthesis example 6
The synthesis of N- (9H- fluorenes -9- bases) acetamide
In the reactor add 0.2mmol fluorenes, 0.04mmol acetate dihydrate manganese, 0.4mmol DDQ, 0.5mL acetonitriles,
0.15mL TFA, mixing, are heated under a nitrogen 120 DEG C, persistently stir 12h, and stopped reaction is cooled to room temperature, adds carbonic acid
Potassium, with ethyl acetate extraction, is dried to neutrality, and vacuum distillation removes solvent, and crude product Jing pillar layer separation obtains final product target product,
Yield 48%.1H NMR(400MHz,CDCl3)：δ 7.61 (d, J=7.5Hz, 2H), 7.49 (d, J=7.4Hz, 2H), 7.33 (t,
J=7.4Hz, 2H), 7.25-7.19 (m, 2H), 6.13 (d, J=8.9Hz, 1H), 5.79 (d, J=8.0Hz, 1H), 2.04 (s,
3H)。
Synthesis example 7
The synthesis of N- benzhydryl pentanamides
0.2mmol diphenyl methanes, 0.04mmol acetate dihydrate manganese, 0.4mmolDDQ, 0.5mL penta are added in the reactor
Nitrile, 0.15mL TFA, 0.35mL DCE mixing, is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to room
Temperature, adds potassium carbonate to neutrality, with ethyl acetate extraction, is dried, and vacuum distillation removes solvent, and crude product Jing pillar layer separation is
Obtain target product, yield 84%.1H NMR(400MHz,CDCl3)：δ 7.25-7.12 (m, 10H), 6.17 (d, J=8.0Hz,
1H), 6.08 (s, 1H), 2.17 (t, J=7.6Hz, 2H), 1.60-1.52 (m, 2H), 1.31-1.24 (m, 2H), 0.83 (t, J=
7.3Hz,3H)。
Synthesis example 8
The synthesis of N- benzhydryl -2- phenyl-acetamides
0.2mmol diphenyl methanes, 0.04mmol acetate dihydrate manganese, 0.4mmolDDQ, 0.5mL benzene are added in the reactor
Acetonitrile, 0.15mL TFA, 0.35mL DCE mixing, is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to
Room temperature, adds potassium carbonate to neutrality, with ethyl acetate extraction, is dried, and vacuum distillation removes solvent, crude product Jing pillar layer separation
Obtain final product target product, yield 70%.1H NMR(400MHz,CDCl3)：δ 7.37-7.27 (m, 9H), 7.24 (d, J=7.2Hz,
2H), 7.08 (d, J=7.2Hz, 4H), 6.23 (d, J=8.3Hz, 1H), 6.04 (s, 1H), 3.64 (s, 2H).
Synthesis example 9
The synthesis of N- benzhydryl Benzoylamides
0.2mmol diphenyl methanes, 0.04mmol acetate dihydrate manganese, 0.4mmolDDQ, 0.5mL benzene are added in the reactor
Formonitrile HCN, 0.15mL TFA, 0.35mL DCE mixing, is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to
Room temperature, adds potassium carbonate to neutrality, with ethyl acetate extraction, is dried, and vacuum distillation removes solvent, crude product Jing pillar layer separation
Obtain final product target product, yield 57%.1H NMR(400MHz,CDCl3)：δ 7.82 (d, J=7.6Hz, 2H), 7.51 (t, J=
7.3Hz, 1H), 7.43 (t, J=7.6Hz, 2H), 7.36-7.28 (m, 10H), 6.69 (s, 1H), 6.46 (d, J=7.8Hz,
1H)。
Synthesis example 10
The synthesis of N- benzhydryl isobutyramides
0.2mmol diphenyl methanes are added in the reactor, and 0.04mmol acetate dihydrate manganese, 0.4mmolDDQ, 0.5mL is different
Butyronitrile, 0.15mL TFA, 0.35mL DCE mixing, is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to
Room temperature, adds potassium carbonate to neutrality, with ethyl acetate extraction, is dried, and vacuum distillation removes solvent, crude product Jing pillar layer separation
Obtain final product target product, yield 75%.1H NMR(400MHz,CDCl3)：δ 7.33-7.27 (m, 5H), 7.22 (t, J=7.5Hz,
5H), 6.24 (d, J=7.9Hz, 1H), 6.09 (s, 1H), 2.46-2.39 (m, 1H), 1.19 (s, 3H), 1.17 (s, 3H).
Synthesis example 11
The synthesis of N- ((4- chlorphenyls) (phenyl) methyl) acetamide
In the reactor add 0.2mmol 1- benzyl -4- chlorobenzenes, 0.02mmol acetate dihydrate manganese, 0.24mmol DDQ,
0.15mL acetonitriles, 0.15mL TFA, 0.35mL DCE mixing, are heated under a nitrogen 70 DEG C, persistently stir 12h, stopped reaction,
Room temperature is cooled to, adds potassium carbonate to neutrality, with ethyl acetate extraction, be dried, vacuum distillation removes solvent, crude product Jing post color
Spectrum separation obtains final product target product, yield 93%.1H NMR(400MHz,CDCl3)：δ7.32-7.26(m,5H),7.18-7.13(m,
4H), 6.25 (d, J=7.0Hz, 1H), 6.18 (d, J=7.8Hz, 1H), 2.05 (s, 3H).
Synthesis example 12
The synthesis of N- (double (4- fluorophenyls) methyl) acetamide
Add 0.2mmol double (4- fluorophenyls) methane, 0.04mmol acetate dihydrate manganese in the reactor, 0.4mmol DDQ,
0.15mL acetonitriles, 0.15mL TFA, 0.35mL DCE mixing, are heated under a nitrogen 90 DEG C, persistently stir 12h, stopped reaction,
Room temperature is cooled to, adds potassium carbonate to neutrality, with ethyl acetate extraction, be dried, vacuum distillation removes solvent, crude product Jing post color
Spectrum separation obtains final product target product, yield 86%.1H NMR(400MHz,CDCl3)：δ 7.18-7.15 (m, 4H), 7.01 (t, J=
7.9Hz, 4H), 6.19 (d, J=7.7Hz, 1H), 6.06 (s, 1H), 2.05 (s, 3H).
Synthesis example 13
The synthesis of N- ((4- fluorophenyls) (phenyl) methyl) acetamide
In the reactor add 0.2mmol 1- benzyl -4- fluorobenzene, 0.04mmol acetate dihydrate manganese, 0.4mmol DDQ,
0.5mL acetonitriles, 0.15mL TFA, mixing is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to room temperature,
Add potassium carbonate to neutrality, with ethyl acetate extraction, be dried, vacuum distillation removes solvent, and crude product Jing pillar layer separation is obtained final product
Target product, yield 85%.1H NMR(400MHz,CDCl3)：δ7.33-7.26(m,3H),7.19-7.15(m,4H),6.99
(t, J=8.6Hz, 2H), 6.35 (d, J=7.1Hz, 1H), 6.19 (d, J=8.0Hz, 1H), 2.02 (s, 3H).
Synthesis example 14
The synthesis of N- hexichol pivaloyl amines
0.2mmol diphenyl-methanes, 0.04mmol acetate dihydrate manganese, 0.4mmolDDQ, 0.5mL front three are added in the reactor
Base acetonitrile, 0.15mL TFA, 0.35mL DCE mixing, is heated under a nitrogen 90 DEG C, persistently stirs 12h, stopped reaction, cooling
To room temperature, add potassium carbonate to neutrality, with ethyl acetate extraction, be dried, vacuum distillation removes solvent, crude product Jing column chromatography point
From obtaining final product target product, yield 51%.1H NMR(400MHz,CDCl3):δ=7.32-7.26 (m, 5H), 7.24-7.19 (m,
5H), 6.22 (d, J=7.4Hz, 1H), 6.16 (d, J=17.5Hz, 1H), 1.24 (s, 9H).
Synthesis example 15
The synthesis of the phenyl ring propyl formamides of N- bis-
0.2mmol diphenyl-methanes, 0.04mmol acetate dihydrate manganese, 0.4mmolDDQ, 0.5mL ring third are added in the reactor
Nitrile, 0.15mL TFA, 0.35mL DCE mixing, is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to room
Temperature, adds potassium carbonate to neutrality, with ethyl acetate extraction, is dried, and vacuum distillation removes solvent, and crude product Jing pillar layer separation is
Obtain target product, yield 94%.1H NMR(400MHz,CDCl3):δ=7.37-7.33 (m, 4H), 7.29 (d, J=11.1Hz,
6H), 6.29 (d, J=7.9Hz, 1H), 6.22 (d, J=6.9Hz, 1H), 1.47-1.40 (m, 1H), 1.04-1.01 (m, 2H),
0.79–0.75(m,2H)。
Synthesis example 16
The synthesis of N- hexichol acrylamides
0.2mmol diphenyl-methanes, 0.04mmol acetate dihydrate manganese, 0.4mmolDDQ, 0.5mL propylene are added in the reactor
Nitrile, 0.15mL TFA, 0.35mL DCE mixing, is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to room
Temperature, adds potassium carbonate to neutrality, with ethyl acetate extraction, is dried, and vacuum distillation removes solvent, and crude product Jing pillar layer separation is
Obtain target product, yield 96%.1H NMR(400MHz,CDCl3):δ=7.28 (d, J=7.4Hz, 2H), 7.23-7.17 (m,
8H), 6.30-6.26 (m, 2H), 6.13-6.07 (m, 2H), 5.64 (d, J=10.2Hz, 1H).
Synthesis example 17
The synthesis of N- (1- phenylethyls) acrylamide
In the reactor add 0.2mmol ethylbenzene, 0.04mmol acetate dihydrate manganese, 0.4mmol DDQ, 0.5mL acrylonitrile,
0.15mL TFA, 0.35mL DCE mixes, and 90 DEG C are heated under a nitrogen, persistently stirs 12h, and stopped reaction is cooled to room temperature,
Add potassium carbonate to neutrality, with ethyl acetate extraction, be dried, vacuum distillation removes solvent, and crude product Jing pillar layer separation is obtained final product
Target product, yield 43%.1H NMR(400MHz,CDCl3):δ=7.2-7.19 (m, 5H), 6.21 (d, J=16.9Hz, 1H),
6.03 (dd, J=16.9,10.3Hz, 1H), 5.90 (s, 1H), 5.57 (d, J=10.2Hz, 1H), 5.16-5.09 (m, 1H),
1.46 (d, J=6.9Hz, 3H).
Synthesis example 18
The synthesis of N- (phenyl (o-tolyl) methyl) acetamide
In the reactor add 0.2mmol 1- benzyl -2- methylbenzene, 0.04mmol acetate dihydrate manganese, 0.4mmol DDQ,
0.5mL acetonitriles, 0.15mL TFA, mixing is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to room temperature,
Add potassium carbonate to neutrality, with ethyl acetate extraction, be dried, vacuum distillation removes solvent, and crude product Jing pillar layer separation is obtained final product
Target product, yield 81%.1H NMR(400MHz,CDCl3):δ=7.29 (t, J=7.2Hz, 2H), 7.24-7.13 (m, 6H),
7.10-7.08 (m, 1H), 6.39 (d, J=8.0Hz, 1H), 6.13 (s, 1H), 2.27 (s, 3H), 2.00 (s, 3H).
Synthesis example 19
The synthesis of N- (phenyl (tolyl) methyl) acetamide
In the reactor add 0.2mmol 1- benzyl -3- methylbenzene, 0.04mmol acetate dihydrate manganese, 0.4mmol DDQ,
0.5mL acetonitriles, 0.15mL TFA, mixing is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to room temperature,
Add potassium carbonate to neutrality, with ethyl acetate extraction, be dried, vacuum distillation removes solvent, and crude product Jing pillar layer separation is obtained final product
Target product, yield 83%.1H NMR(400MHz,CDCl3):δ=7.40-7.27 (m, 6H), 7.15-7.06 (m, 3H), 6.27
(brs,2H),2.38(s,3H),2.10(s,3H)。
Synthesis example 20
The synthesis of N- (phenyl (p-methylphenyl) methyl) acetamide
In the reactor add 0.2mmol 1- benzyl -4- methylbenzene, 0.04mmol acetate dihydrate manganese, 0.4mmol DDQ,
0.5mL acetonitriles, 0.15mL TFA, mixing is heated under a nitrogen 90 DEG C, persistently stirs 12h, and stopped reaction is cooled to room temperature,
Add potassium carbonate to neutrality, with ethyl acetate extraction, be dried, vacuum distillation removes solvent, and crude product Jing pillar layer separation is obtained final product
Target product, yield 88%.1H NMR(400MHz,CDCl3):δ=7.33-7.27 (m, 3H), 7.22 (d, J=7.1Hz, 2H),
7.12 (t, J=6.2 Hz, 4H), 6.20 (d, J=8.0 Hz, 1H), 6.12 (d, J=7.0 Hz, 1H), 2.32 (s, 3H),
2.04(s,3H)。
Claims (9)
1. a kind of method that amide is prepared by arylmethane derivant and nitrile, comprising following step：
Arylmethane derivant, nitrile compounds, Mn catalyst, oxidant, TFA, solvent are placed in reaction vessel, are mixed,
Under nitrogen atmosphere, at reaction temperature is for 70～90 DEG C, 8～16h of stirring reaction is continued, reaction is cooled to room temperature after terminating,
Add potassium carbonate to neutrality, then extracted with organic solvent, be dried, vacuum distillation concentration removes solvent, crude product Jing column chromatography
Separate, amides compound is obtained final product, with following structural formula：
In the structure Formulas I, R1It is aryl, fat-based, hydrogen；R2It is methyl, normal-butyl, isopropyl, the tert-butyl group, cyclopropyl, ethylene
Base, benzyl, phenyl.
2. the method that amide is prepared by arylmethane derivant and nitrile according to claim 1, it is characterised in that described
Mn catalyst is at least one in manganese acetate and acetate dihydrate manganese.
3. the method that amide is prepared by arylmethane derivant and nitrile according to claim 1, it is characterised in that described
Nitrile compounds are at least in acetonitrile, valeronitrile, isopropyl cyanide, trimethylacetonitrile, cyclopropylniitrile, acrylonitrile, benzonitrile, benzene acetonitrile
Kind.
4. the method that amide is prepared by arylmethane derivant and nitrile according to claim 1, it is characterised in that described
Oxidant is the chloro- 5,6- dicyanos -1,4- benzoquinone (DDQ) of 2,3- bis-.
5. the method that amide is prepared by arylmethane derivant and nitrile according to claim 1, it is characterised in that the virtue
Methylmethane derivant is selected from diphenyl methane, ethylbenzene, isobutyl-benzene, indane, fluorenes, 1,2,3,4- naphthanes, 1- benzyl -4- chlorine
Benzene, double (4- fluorophenyls) methane, 1- benzyl -4- fluorobenzene, 1- benzyl -4- methoxybenzenes, 1- benzyl -4- ethylo benzenes, 1- benzyl -2-
Methylbenzene, 1- benzyl -3- methylbenzene.
6. the method that amide is prepared by arylmethane derivant and nitrile according to claim 1, it is characterised in that described anti-
Additive is trifluoroacetic acid (TFA) during answering.
7. the method that amide is prepared by arylmethane derivant and nitrile according to claim 1, it is characterised in that described anti-
At least one of the solvent in acetonitrile, 1,2- dichloroethanes (DCE) and toluene during answering, when acetonitrile solvent is, its
Serve as reaction reagent.
8. the method that amide is prepared by arylmethane derivant and nitrile according to claim 1, it is characterised in that manganese is catalyzed
Mol ratio between agent, DDQ oxidants, trifluoroacetic acid, nitrile compounds and arylmethane derivant is [0.1～0.3]：[1.0
～3.0]：[15～25]：[15～50]：1, reaction temperature is 70～90 DEG C, and the response time is 8～16h.
9. the method that amide is prepared by arylmethane derivant and nitrile according to claim 1, it is characterised in that the extraction
It is ethyl acetate, chloroform or dichloromethane to take the organic solvent in step.
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