SU365362A1 - METHOD OF OBTAINING N-ARYLIMIDES 0,0-DIALKYL- - Google Patents

Description

one

This invention relates to the field of organophosphorus compounds, namely, to a method for producing "new H-arylim, and having 0.0-alkyl-0-l-hydroxyarylphos; flutes or diaryl-0-n01xyarylphosph" nit, 01 in the general formula

HE

(one)

/

where R is alkoxy or aryl; Ai is aryl.

A known method for the preparation of 4-al: Cox-yaroyl esters of dialkylphosphoric acids by the interaction of trialkylphosphites with l-quinones. The interaction of triarylphosphones with l-quinones is also known. However, amidophosphines in the reaction with p-hino, we have previously} ie were involved. The resulting interactions of the compounds of this formula can be used as intermediates (4 products for the synthesis of biologically active substances.

The proposed method for the preparation of N-arylimides with 0.0-1 dialkyl-O-l-o.xyarylphosphine tov or diaryl-0-d-hydroxyarylphosphine 1 -nites is that 0,0-dialkyl-E-aryl-oophosphites or diaryl M-arylamidophosphines are reacted with p-hione in

2

environment of an inert organic solvent, such as sulfuric ether, at room temperature.

The yield of the products is 74-90%. Their structure is confirmed by IR spectra.

In the IR spectra of the products obtained, there is an intense absorption, characteristic of a phosphimide bond with a maximum at 1320 SL1-1, P-O-C - alkyl - 1030-1060 cm - P-O-C-aryl group 1100 s. , the benzene core of 1600–1620 sig-, 1500–1520 cm — hydroxyl group 2400–3200 SL1-1.

Example 1. To 21.3 g (0.1 g-mol of N-phenylamide diethylphosphorous acid in 150 L1L of dry ether is added in portions of 10.8 g (0.1 g-mol) of l-quinone. The reaction mixture is stirred 30 min at room

temperature The resulting crystalline product is filtered off. Obtain 29 g (90%) of 0, 0-diethyl-0-l-hydroxyphenyl-K1-phenylimidophosphite with so pl. 98 ° C (recrystallized from ether).

Found,%: P 9.70; N 4.36. Ci6H2oNO4P.

Calculated,%: P 9.65; 4.36. Example 2. To 4.5 g (0.02 g-mol) tolyl amide diethylphosphorous acid in 30 ml

sulfuric ether was added 2.1 g (0.02 g- / iol &)

3

p-quinone. The reaction mixture is stirred at 10 niH at a pitched temperature. O. The formed crystalline product is filtered off. Obtain 5.2 g (84.7%) of 0, 0-dipethyl-p-hydroxyphenyl-K-tolylimidophosphite with m. Pl. 1: 13 ° C (from ether).

Found,%: P 9.47; N 4.56.

C.rHaaNOiP.

Calculated.,%; R 9.25, N 4.12.

When ep 3. To 5.4 g {0,022 g-mol) N-phenylamide dibutyl phosphorous acid in 30 ml of the seroether add 2.1 g p-hyion. The reaction mixture is stirred at room temperature for 60 minutes. The solvent is removed: under reduced pressure. After recrystallization from sulfuric ester, 5.7 g (76%) of 0,0-dibutyl-0- -0 | xyphenyl.Phenylimidophosphite with m.p. 73 ° C.

Found,%; P 8.64; N 3.90. C7 Jb8NO..P.

Calculated,%: P 8,22; N 3.72. : Example 4. To 5.6 g (0.02 g-mol) of M-phenylamide of definylphosphonic acid in 50 l {l of dry sulfuric ester is added 2.1 g (0.2 g-mol) of p-quinone. The reaction mixture is stirred for 30 minutes at campat temperature in a stream of dry nitrogen. Formed

four

the crystalline product is filtered off. T. nl. 10G-107 ° C. 6.4 g (74%) of 0,0-d-ifeyl-0- / g-hydroxyphenyl-N-phenyl-imidophosphinite were obtained.

Found,%: P 8.52; N 3.64.

CoJiioNOaP.

Calculated,%: P 8.00; N 3.93.

Subject invention

. The method of obtaining N-arylimides 0,0-;

0,0-di, it is to obtain 1-arylimid; yl-0-l-szhsarylphosphito.z or diaryl-0 alkyl-0-l-sgsyarylphosphito.z or diar p5 total for1 oxyarylphosphonates of the general formula

,

(B) N-.

where R-alkoxyl or aryl; Ar - aryl, ili4a oii {uuiH, 410 0,0-dpalkyl-N-arylamidophosphigill ill dparpl-M-arplam1 Dosfip is subjected to interaction with c-gipon in an inert organic solvent, pair: 1 meter sulfuric ether, followed by separation of non-sulfur product known reception MP.