The catalyst for producing 1,2-bis(dialkylamino)-1-arylamino

 

(57) Abstract:

The invention relates to catalysts, in particular to a catalyst for producing 1,2-bis(dialkylamino)-1-arylamino.

The resulting catalyst comprises the product of the interaction douglasthe cobalt, an activator of triphenylphosphine and dialkylaminoalkyl as a reductant, taken in a molar ratio 1:(1,5-2,5):(2-6) respectively. The advantage of the catalyst is its accessibility. table 1.

The invention relates to the field of catalysts, in particular catalysts for production of 1,2-bis(dialkylamino)-1-arylamino (1), which can find application in organic and ORGANOMETALLIC synthesis.

Known two-component catalyst /g Dozzi, S. Sisia, A. Mazzei. J. Organometal. chem. , 164 (1979) 1-10/ for dialuminium compounds, namely 1,4-bis(dialume)-2-methylbutane consisting of titanzincoated Cf2iCl2(Cf =5-C5H5) and amine complex of aluminum hydride (AN3N(CH3)3.

The disadvantage is the inaccessibility of one of the catalyst components (Cf2TS2), which in the country is produced and synthesized on the basis of parodie:

a) C5H6+Na(5-C5H5)Na+H2< / BR>
b) TiCl4+(5-C5H5)Na(5-C5H5)2TiCl2+NaCl

In addition, a known catalyst is not possible to obtain 1,2-bis(dialkylamino)-1-arylidene (1).

Known two-component catalyst /U. M. Dzhemilev, A. G. Ibragimov, M. N. Ergaliev, R. P. Muslumov. WPI. An. The series of chem., 1995, 8, 1561-1567/ for dialuminium compounds, namely 1,4-bis(ditylum)-TRANS-2,3-dialkylamino consisting of zirconatetitanate (Cf2Zr12and diethylaluminium Et2AS.

The disadvantage is the inaccessibility of one of the catalyst components (Cf2ZrCl2), which in the country is not performed; in addition, a known catalyst is not possible to obtain 1,2-bis(dialkylamino)-1-arylidene (1).

A new catalyst to obtain 1,2-bis(dialkylamino)-1-arylamino (1).

The proposed catalyst is available douglasthe cobalt (So2), an activator of triphenylphosphine (PH3R) and dialkylaminoalkyl R2AS, where R= Et, n-VI, taken in a molar ratio So2:Ph3P: R2AlCl= 1:(1,5-2,5):(2-6). The role of R2AS ZackR with the formation of the active complex.

In the presence of the specified catalyst formed 1,2-bis-(dialkylamino)-1-arylidene (1) outputs 72-88%. The reaction is carried out in an inert atmosphere by the interaction of aillein (styrene, para-methylstyrene) with dialkylaminoalkyl (R2AS, where R= Et, n-VI) and magnesium (powder), taken in a molar ratio of R2AS:MD=10:20:10 at a temperature of 21-22oWith in tetrahydrofuran (THF) for 8 hours according to scheme 1 (see the end of the description).

The amount of catalyst required for the reaction is 2 to 6 mol % relative to the original aillein.

Differences between the proposed catalyst from the famous.

Components of the proposed catalyst are manufactured in the country duplissy cobalt (So2), available activator (PH3P) and the reducing agent R2AS.

The invention is illustrated in the examples.

Example 1. Preparation of catalysts. In a glass reactor with a volume of ~50 ml installed on a magnetic stirrer, an argon atmosphere was placed 0.4 mmol SOS2, 0.8 mmol of RH3R, 5 ml of dry THF and at a temperature of -5oWith added dropwise 1.6 mmol Et2AS. Premesis the catalyst added at -5oTo the reaction mass, consisting of 10 mmol of fresh styrene 10 mmol magnesium powder and 20 mmol Et2AS in 10 ml of dry THF, stirred for 8 hours at a temperature of 21-22oC.

Get 1,2-bis(ditylum)-1-Penilaian exit 81%.

The yield of the target product (1) is determined using GC by analysis of the hydrolysis products. Products lateralize confirm receipt of the target product (1). When the hydrolysis of 1,2-bis(ditylum)-1-phenylethane (1) is formed ethylbenzene (2), and when lateralize respectively 1,2-dematerializer (3) of scheme 2 (see the end of the description).

Spectral characteristics of ethylbenzene (2): So Kip. 135-136oS, nD221.4950. IR spectrum (V, cm-1):690, 735, 1020, 1450, 1490, 1590, 2850, 3005, 3025. An NMR spectrum1N(, m D.):1.17 (t, 3H, CH3, J=7,6 Hz), 7.12-7.22 (m, 5H, CH-arene). An NMR spectrum13C, M. D., CDCl3):15.62 (WITH1), 28.97 t (2), 144.29 (WITH3), 127.96(WITH4), 128.32(WITH5), 127.88(WITH6).

The spectral characteristics of the 1,2-dematerialise (3): So Kip. 136-137oS, nD201.4958. IR spectrum (V, cm-1):690, 730, 1020, 1450, 1500, 1600, 2170 (VC-D), 2850, 3020. An NMR spectrum1N(, m D.):1.19 (1, 2H, CH2D, J=7,6 Hz), 7.08-7,27 (m, 5H, CH-arene). An NMR spectrum13P>5), 127.88 (WITH6).

Other examples of the invention, shown in the table.

The catalyst was prepared in THF at a temperature of -5oC, the reaction of 1,2-dialuminium of arylolefins was carried out at room temperature (21-22o(C) within 8 hours.

The catalyst for producing 1,2-bis(dialkylamino)-1-arylamino obtained by the interaction douglasthe cobalt (CoCl2), adjuvants triphenylphosphine (PH3R) and dialkylaminoalkyl (R2ll, where R= Et, n-Bu) as a reducing agent in the following molar ratio of the components: ol2: PH3R: R2ll= 1: (1,5-2,5): (2-6).

 

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