Microwave-Assisted and Phase Transfer Catalysis Synthesis of Tris(2-Cyanoethyl)Amine

doi:10.7517/j.issn.1674-0475.2004.04.293

Abstract

Abstract: The technology of combining microwave irradiation with phase transfer catalysis was applied to organic synthesis.The intermediate of a ligand tris(2-cyanoethyl)amine was synthesized by the reactions of ammonia water and acrylonitrile in the pressure termetic pot under microwave irradiation.The reaction was completed in 61.2%(weight) yield,and the reaction time was 8 times shorter than the traditional method.The reaction was 67.2%(weight) yield,and the time was shortened by 90 times under microwave irradiation.The product was characterized by elemental analysis,IR,¹H-NMR,ES-MS,and TG-DTA.

Key words: tris(2-cyanoethyl)amine, high pressure hermetic seal, phase transfer catalysis, microwave-promoted, characterization

CLC Number:

TQ57

NIE Guo-chao. Microwave-Assisted and Phase Transfer Catalysis Synthesis of Tris(2-Cyanoethyl)Amine[J]. Imaging Science and Photochemistry, 2004, 22(4): 293-297.

References

[1] Hassan Keypour, Sadegh Salehzadeh, Paresh R V. Synthesis of two potentially heptadentate (N4O3) schiff-base ligands derived from condensation of tris(3-amimopropyl)amine and Salicyaldehyde or 4-Hydroxysalicylaldehyde. Nickel(Ⅱ)and copper(Ⅱ) complexes of the former ligand[J]. Molecules,2002,7:140-144.
[2] Hassan Keypour, Sadegh Salehzadeh, Pritchard R G, Parish R V. Synthesis and crystal structure determination of a nickel (Ⅱ) complex of an acyclic pentadentate (N5) mono schiff base ligand[J]. Molecules,2001,6:909-914.
[3] Hassan Keypour, Sadegh Salechzadeh, Pritchard R G, Parish R V. Nickel (Ⅱ) complexes of fully and partially condensed schiff-base ligands derived from tris (3-aminopropyl)amine and acetylpyridine[J]. Transition Metal Chemistry, 1998,23 (5): 605-608.
[4] Hassan Keypour, Pritchard R G, Parish R V. Isolation of temary complex precursors and partially condensed intermediates to macrocyclic complexes of nickel (Ⅱ) and copper (Ⅱ)[J]. Transition Metal Chemistry, 1998, 23(5): 609614.
[5] Boon J M, Lambert T N. Smith B D, Beatty A M, Ugrinova V, Brown S N. Structure/activity study of tris (2-aminoethyl)amine-derived translocases for phosphatidylcholine[J]. J. Org. Chem.,2002,67(7):2168-2174.
[6] Kwak J, De Capua A, Locardi E, Goodman M. TREN (tris (2-aminoethyl)amine):an effective scaffold for the assembly of triple helical collagen mimetic structures[J]. J. Am. Chem. Soc.,2002,124(47):14085-14091.
[7] 张江润,杨绪杰,陆路德,汪信,许兴友Tren缩三(邻苯甲酰基乙基醚)胺穴合物的合成及表征[J].淮海工学院学报,2002,11(1):45-47Zhang J R. Yang X J, Lu L D, Wang X, Xu X Y. Synthesis and characterization of a series of chelated complexes N(CH₂CH₂-O-C₆H₄-CH = NCH₂CH₂)₃N[J]. Journal of Huaihai Institute of Technology, 2002,11 (1): 45-47.
[8] Kopet G J M, Van Genderen M H P, Elissen-Roman C, et al. Protonation mechanism of poly(propylene imine) dendrimers and some associated oligo amines[J]. J. Am. Chem. Soc., 1997,119:6512-6521.
[9] 许兴友,孙桂进,高健,等.三(2-氰乙基)胺的合成与表征[J].淮海工学院学报,2003,12(2):32-34. Xu X Y, Sun G J, Gao J, et al. The synthesis and characterization of tris (2-nitrilethyl)amine[J]. Journal of Huaihai Institute of Technology, 2003,12(2): 32-34.
[10] 梅光泉.β,β′,β"-三氨基三乙基胺合成方法的改进[J]赣南师范学院学报,2002,(3):55-56.Mei G Q. An Improved method for the preparation of β,β′,β″ - triaminotriethylamine[J]. Journal of Gannan Teachers College,2002, (3):55-56.
[11] Larhed M, Hallberg A. Microwave-assisted high-speed chemistry: a new technique in drug discovery[J]. Drug Discov Today,2001;6(8):406-416.
[12] Strauss C R. A combinatorial approach to the development of environmentally benign organic chemical transformations[J]. Aust. J. Chem., 1999,52,83-96.
[13] Giguere R J, Bray T L, Duncan S M, Majetich G. Application of commercial microwave ovens to organic synthesis[J].Tetrahedron Lett., 1998,27 (41): 4945-4948.
[14] David Adam. Designer microwave ovens that can heat reactants in record time are heralding a quiet revolution in chemical synthesis[J]. Nature, 2003,421: 571-572.
[15] Simon J. Gaskell. Electrospray: principles and practice[J]. J. Mass Spectrom, 1997,32: 677-688.
[16] 王静,姜凤超微波有机合成反应的新进展[J].有机化学,2002,22(3):212-219.Wang J, Jiang F C. Recent development of microwave induced organic reaction[J]. Chinese Journal of Organic Chemistry, 2002,22(3): 212-219.
[17] 苏跃增,孙晓娟,刘萍.关于微波化学反应机理的探讨[DB/OL][J]化学通报(网络版),2000,(3):http:∥hxtb. icas. ac. cn/col/2000/c00004. htm.Su Y Z, Sun X J, Liu P. The probe into the mechanism of microwave chemical reaction[DB/OL][J]. Chemistry Online, 2000, (3): http:∥hxtb. icas. ac. cn/col/2000/c00004. htm