SU998464A1 - Process for producing 2-dialkylamino-2-(2-alken-1-yl)-1,3-benzodioxoles - Google Patents

Description

This invention relates to a process for the preparation of new compounds of the formula

RI

01l2CH C

 g

0 N (R) 2

where R is lower alkyl;

R is a hydrogen atom or methyl;

 lower alkyl,

which possess fungicidal activity.

A known method for producing 2-methyl-2-ETOXI-1, 3-benzodioxole by reacting pyrocatechin with ethoxyethine when heated in the presence of mercury chloride in an alkaline medium l.

However, under these conditions, 2-dialkylamino-2- (2-alkene-1-yl) -1,3-benzodioxoles cannot be obtained.

The purpose of the invention is the preparation of 2-dialkylamino-2- (2-alkene-1-yl) -1.3 benzodioxoles having fungicidal activity.

The goal is achieved in a manner that is that the pyrocatechin is reacted with

1-dialkylamino-3-alkene-1-other formula

BUT

C SNSSL / (n), (,,)

R have the indicated values R, R. chen,

in the environment of inert organic solvent of the solvent, at ambient temperature.

Absolute diethyl ether is preferably used as the inert organic solvent.

15

The structure of the synthesis products was established on the basis of PMR spectroscopy data. In the PMR spectrum of 2-diethylamino-2- (2-buten-1-yl) -1,3-benzodioxole, the unsaturated fragment

20 LAN

CH -CH CH-CHl - belongs to the following signals: the signal of the protons of the methyl group Hp is represented by a double-doublet (f 1.51;: methylene rpyMffa

Claims (2)

The 25 protons of Hp are represented by the doublet (f 2.63; the vinyl protons of Nd and Hg belong to the multiplet (f5,13–5,43. The signals of the hydrogen nucleus of the benzene ring are represented by a signal in the region of 306 f6,38. and quartet (f 2.52. Example 1. Preparation of 2-diethylamino-2- (2-buten-1-yl) -1,3-benzodioxole. To a solution of 13.7 g (0.1 mol) of 1-diethylamino A solution of 11 g (0.1 mol) of pyrocatechin in 35-40 ml of absolute ether is added dropwise while stirring 3-penten-1-in in 50 ml of absolute ether. Heat evolution is observed. After 10-15 minutes the solvent is removed under vacuum, 2-diethylamino-2- (2-buten-1-yl) -benzodioxole is distilled under vacuum. Yield: 17.3 g (70%); boiling point (0.0bmm.str.); , 5200. Elemental analysis for C N., N0: le 2-1 2. Found,%: C 72.75-72.70; H 8.62-8.60; N 5.70-5.73. Calculated ,%: C, 72.84; And, 8.56; N, 5.66. 2. Preparation of 2-diethylamino-2- (3-methyl-2-buten-1-yl) 1, 3-benzodioxole. Analogously to example 1, using a solution of 1-diethylamino-4-methyl-3-pentzn-1-yna, 2-diethylamino-2- (3-methyl-2-buten-1-yl) -1.3 benzene dioxole is obtained. . .Outlet 18.3 g (73%); bp 8990 С (0.03 mm Hg); 1,0154; P2o 1.5168.Element analysis for C, 6 Hj N0: Found,%: C 73.48-73, 42; H 8.90-8.98; N 5.42-5.34. th number,%: C 73.53; H 8.87: N 5.36. You are about 2 pi pifo gd in ra ma pr ma c. The proposed method provides high yield and purity of the products obtained. The invention The method for producing a 2-dialkylamino (2-alkene-1-yl) -1,3-benzodioxole formula of the formula is lower alkyl; is a hydrogen or methyl atom; R is lower alkyl, distinguished by the fact that rocatechol is reacted with 1-dialkylamino-3-alkene-1-other rmuly:,). e R, R1 and K have the indicated values, inert organic medium medium at ambient temperature. Sources of information, which are taken into account in the examination of l.Viehe H.G.Chemistry of Acetylenes reel Dekker N. iy, 1969, 779.