SU1366511A1 - Method of obtaining benzol-1,4-bis-diazonium of bromide - Google Patents

Abstract

The invention relates to diazonium compounds, in particular the preparation of benzene-1,4-bis-diazonium bromide (DB), an intermediate for the synthesis of dyes and active substances. The goal is to create a new method of producing useful intermediates. Synthesis of DBs is carried out by brominating bis (0,0-dialkyl-phosphoryl) hydrazone 1,4-benzoquinone with bromine in acetonitrile or acetone at 5 -. The method makes it possible to obtain target DBs in one stage under mild conditions from the available reagents with a yield of 63–94%.

Description

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Example4. To a solution of 3.0 g (0.0073 mol) of bis- (0,0-diethylphosphoryl) -dihydrazone of 1,4-benzoquinone in 30 ml of dry acetonitrile was added 2.35 g (O, mol) of bromine. The mixture is melted for 72 hours at.

The resulting precipitate is filtered, washed with 10 ml of acetonitrile, dried.

Benzene-1,4-bis-diazonium bromide B-2, O g (94%) of benzene-1,4-bis is obtained as a highly reactive substance and can be used as an intermediate for the synthesis of dyes, biologically active

The invention relates to organic and organophosphorus chemistry, namely to a method for producing benzene-1,4-bis-diazonium bromide of the formula

BrN, Q-N2Br

bottom of bromide.

Example5. To a solution of 5.2 g (0.0130 mol) of bis- (0,0-diethylphosphoryl) dihydrazone-1,4-benzoquinone in 15 to 40 ml of dry acetonitrile was added 4.1 g (0.0260 mol) of bromine. The mixture is defended for 72 hours at 25 seconds. Then proceed as in Example I. 3.4 g (91%) of benzene are obtained. 1, 4-bis-dia. The invention is illustrated by the following bromide.

Examples. To a solution of 4.9 g

Example 1. To a solution of 3.0 g (0,0120 mol) of bis- (0,0-diethylphosphoryl) 1,4-benzoquinone dihydrogenase in 40 ml of dry acetonitrile was added 25 4.0 g (0.0250 mol ) bromine. Subsequent operations are carried out as in Example 1; 3.26 g (93%) of benzene-1I-bis-diazonium bromide are obtained.

Example7. To a solution of 3.0 g. All operations are carried out in an atmosphere of ar-Q (0.0073 mol) of bis- (0,0-diethylphosphogon). 2.0 g (94%) of benzene-yl) dihydrazone are obtained. 1,4-benzoquinone in

30 ml of dry acetonitrile are added 2.6 g (0,0162 mol) of bromine. Subsequent operations are carried out as in Example 1. ,, g 1.9 g (89%) of benzene-1,4-bis-diazonium bromide is applied.

Example To a solution of 4.9 g (0.0120 mol) of bis- (0, O-diethylphosphoric 1) -dihydrazone of 1,4-benzoquinone in (0.015 mol) of bromine with a solution of 3.5 g of 40 ml of dry acetonitrile is added (0 , 0075 mol) bis- (d, 0-diisopropyl) 2.6 g (0.0162 mol) of bromine. Subsequent operations are carried out as in Example 1. 3.2 g (91%) of benzene-1,4-bis-diazonium bromide are obtained.

The IR spectra of benzene-1,4-bis-diazonium bromide are taken in petroleum jelly. The IR spectra show the presence of an intense N-N band (2200) and benzene ring bands (1590 cm), the other bands are in the 1270, 1120, 1020, 730, 520 cm regions.

Thus, the proposed compounds, additives that improve the physico-chemical properties of polymers.

The purpose of the invention is to develop a new method of obtaining a new compound.

(0.0073 mol) of bis- (0,0-diethylphosphoryl) -dihydrazone of 1,4-benzoquinone in 30 ml of dry acetonitrile was added 2; 3 g (0.01646 mol) of bromine. The mixture is defended for 70.h at 30 C.

The precipitate formed is filtered, washed with 10 ml of acetonitrile, and dried.

1,4-bis-diazonium bromide. Received

the substance has a mp, 46-48 C.

Found,%: From 23.60; H 1.31; Br 4.42; N 19.09.

C, H, Rr, N,

Calculated,%: C 24.65; H 1.37; Br 54.79; N 19.18.

PRI mme R 2. Shift 2.4 g

dihydrazone 1,4-benzoquinone in 40 ml of dry acetonitrile. The mixture is settled for 96 h at 5 ° C.

With the precipitate formed, 45 operations were carried out as in Example 1. 1.7 g (90%) of benzene-1,4-bis-diazonium bromide was obtained.

Example To a solution of 3.5 g (0.0075 mol) of bis- (0,0-isopropylphosphoryl) dihydrazone I, 4-benzoquinone in 40 ml of dry acetone, 2.6 g (0.0655 mol) of bromine are added. The mixture is defended for 72 hours at 5 ° C.

The precipitate formed is filtered and washed with 15 ml of dry acetone, dried. All operations are carried out in the atmosphere.

This allows you to get a new connection in one stage with a high yield of 63-94%. In this case, the method is not energy intensive, the starting materials are easily accessible. Bis- (0,0-dialkylphosphate 1) dihydroxenes of I, 4-benzoquinone are prepared by argon. 1.38 g (63%) of benzene-1, 4-bis-diazonium bromide are obtained.

This allows you to get a new connection in one stage with a high yield of 63-94%. In this case, the method is not energy intensive, the starting materials are easily accessible. Bis- (0,0-dialkylphosphate 1) dihydroxides of I, 4-benzoquinone get coni13665114

the denaturation of phosphoric hydrazides with an acid, that bis-(0,0-dialkylphosphoryl) dicotone with 1,4-benzoquinone. 1,4-benzoquinone is exposed to

Claims (1)

Claims for booking bromine in acetonite Method for producing benzene-1,4-bisryl or acetone with 5 - diazonium bromide, consisting of - 30 C.