CS226918B1 - Picrates of 2-furylethenic derivatives and method of preparing same - Google Patents

Description

The invention relates to picrates of the 2-furylethene derivatives of the general formula I

where

X is COOCH 3, COCH 3, COOCH 2 CH 3 and

Y is COOCH3, COCH3, COOCH2CH3, and a process for their preparation.

The compounds according to the invention and the process for their preparation have not been described in the literature to date. Only the 5-trimethylammonium bromides of 2-furylethene derivatives are described in AO 221187 by the same authors.

SUMMARY Methods for making compounds according to the invention is that the 5-trimethylammonium-2 furyleténových derivatives of formula II (+) -, (CH ^ n J _[0 JLch = c ^ ^'Sr (II) wherein

X and Y are the same as in formula I, react with picric acid in a medium of water or alcohols C1 to Cs, or the reaction proceeds according to the equation:

in their mixtures within the temperature range of -10 ° C

140 [deg.] C.

OH. % ^N I ^N ° Z

wherein X and Y are the above.

An advantage of the process for the preparation of trimethylammonium salts according to the invention is that the syntheses are one-stage starting from relatively available raw materials.

The compounds of the present invention can serve as intermediates for the synthesis of novel furan derivatives.

Example 1 g of the ammonium salt of formula II wherein X is COOCH2CH3 and Y is COCH3 is dissolved in 50 ml of water and filtered. 2.3 g of picric acid dissolved in 200 ml of water and 50 ml of ethanol are added to the solution thus prepared. The precipitated rye precipitate is filtered off with suction and dried in a desiccator over P2O5. 3 g (60%) of picrate are obtained as a yellow crystalline solid, m.p. t. Mp 184-185 ° C.

IR spectrum measured on spectrophotometer and US-20 KBr technique:

γc-o = 1700 cm ^-1 , 1690 cm ^-1 ;

/ cc - 1640 cm ¹ ;

Zc-oc = 1020 cm ^{@ -1} .

UV spectrum (measured on a UV-VIS in methanol):

Λ _max 293 nm.

1 H NMR Spectrum (measured on a Tesla BS-467, TMS in hexadeuteriodimethylsulfoxide):

Δh = 7.17 ppm;

_δ κ = 7.06 ppm J _3, 4 = 4 Hz;

A < $ h = 7.41 ppm;

< _H $ - 8.59 ppm;

arom H

δα OCH = 4.28 ppm; ? H CH - 1.29 ppm; <5h COCH3 = 2.53 ppm; δα N (CH) 3 - 3.63 ppm.

Example 2 g of an ammonium salt of formula II wherein X is COCH 3 and Y is COCH 3 is dissolved in 200 ml of water and 2.5 g picric acid dissolved in 200 ml of water and 50 ml of methanol is added to the solution thus prepared. The separated crystalline solid is filtered off and dried in a desiccator over P2O5. 2 g of a picrate of the formula I are obtained, wherein X is COCH3 and Y is CHCO3. t. 90 DEG-95 DEG C. (decomposition).

IR spectrum (measured on a UR-20 KBr instrument):

and _C '= o 1695, 1685 cm ^1, VC-C = 1640 cm ^1, VC-OC - 1040 cm ^-1.

UV spectrum (measured on a UV-VIS in methanol):

Λ max - 307 nm.

..... ~

EXAMPLE 1 a d 3

4.5 g of the ammonium salt of formula II wherein X is COOCH3 and Y is COCH3 are dissolved in 100 ml of water. 4 g of picric acid dissolved in 300 ml of water and 100 ml of ethanol are added to the solution thus prepared. The precipitated rye precipitate is filtered off with suction and dried in a desiccator over P2O5. 4.5 g (58%) of the picrate are obtained as a yellow crystalline substance of 11 170 DEG-172 DEG C.

IR spectrum measured on a spectrophotometer (UR-20 KBr technique):

v _c- o = 1700, 1690 cm ^-1 , v _c = c - 1640 cm ^-1 vc-oc 1020 cm

UV spectrum (measured on a UV-VIS in methanol):

And _{m and} x = 291 nm.

Analysis for C 19 H 20 N 4 O 11 (480.4) calculated:

47.50% C 4.19% H 11.65% N found:

* 47.02% C 4.00% H 11.25% N

Example 4 i

From 4.5 g of the ammonium salt of formula II wherein X is COOC2H5 and Y is COOC2H5 is prepared analogously to the previous example. 3.5 g of picrate are obtained as a yellow crystalline solid, m.p. t. Mp 152-157 ° C.

IR spectrum measured on a spectrophotometer! UR-20 KBr technique):

»Co = 1705, 1690 cm ^-1 , i> cc = 1642 cm ^-1 , µc-oc = 1020 cm ^-1 ·.

Analysis for C21H24N4O12 (524.4):

calculated:

% C, 48.05;% H, 4.57;% N, 10.61.

% C, 47.88;% H, 4.44%.

Claims (2)

Claims 1. The 2-furylethene derivatives of formula I wherein X is COOCH 3, COCH 3, COOCH 2 CH 3, and Y is COOCH 3, COCH 3, COOCH 2 CH 5. 2. Process for preparing compounds according to claim 1 characterized in that the 5-trimethylammonium-2 furyleténových derivatives of formula II (+) _{C% N} _jO_ch = c ^ · ^Br (-) wherein X and Y are the same as in Formula I, reacting with picric acid in a C 1 -C 5 water or alcohol medium or mixtures thereof at a temperature range of -10 ° C to 140 ° C.