SU428598A3 - METHOD FOR OBTAINING DERIVATIVE IMIDOCARBONATES - Google Patents

Description

This invention relates to a process for the preparation of new Imido.carbonate Derivatives having biologically active properties.

A known method for the preparation of dithioimidocarblslata total for: multi (

KM S (5Siz) 2,

where R is a sulfoa.rivna rpyinna, substituted by halogen,, gr1y | ppoy, or a: c1-lilamipnoy group, consisting in the fact that methyl ef |

However, the synthesis of new compounds with multiple improved and properties is currently attracting the attention of various researchers.

According to the invention, new imidocarbonate derivatives of the general formula are obtained.

Y-E,

/ L

R-.

scrap, pyridine ring, unsubstituted or substituted by halogen or lower alkyl. with a number of substituents of 1-3;

R is alkyl, unsubstituted or substituted by 01XI by the group, IL, AND alkoxycarbonyl group; alkenyl, adkinyl, ar-alkyl, aromatic ring, 1-ene mesine1: substituted or substituted with 1-4 halon atoms, 1-4 alkylate or nitro group; phenyl; kil substituted by halogen or lower al.quil;

R2 is alkyl substituted by hydroxy group or; and AL | COXYcarbonyl group; alkenpl, aral-kil, aromatic ring, unsubstituted or substituted with 1-4 halogen atoms, 1-4 alkyl, lithocrust or lower alkylene; moreover, when Ar is an unsubstituted benzene ring R,. and R2 are aralkyl radicals of at least one of which are And have a substituent that have better properties than those known.

According to the invention, these compounds are obtained by lengthening the TIIO-carbamipic or dithioharbamic acid esters of the general formula:

where Ar, Y, and RI have the indicated meanings, with haloisrganostera, and I are connected by a common (bop mules

R2-X

where 2 has the specified values, X is a halogen atom.

To carry out the synthesis, to a solution of 1 mol of the derivative THOiKapoaiMHHosoro or dithiocarbally new ester s methanol, ethanol, tetrathydrofuranium, dioxane, dimethylsulfoxide, or dimethylforma. bases (alkali or alkaline earth metal hydroxides, for example, NaOH, KOH, Ca (OH) 2), an alcohol, a NaOCHs nalIMER, or NaOC2H5 or KOCN3) for the neutralization of hydrochloric acid, which is formed during the reaction. You can first add oona-ngi to the solution of the carbamine ester, and then add an organohalide compound, or first add the halo aorga compound, and then the base to the piacTBOpy carbaMinO | V01GO ester. The reaction is carried out with stirring at a temperature from 0 - 100 ° C for 1-4 hours. After the reaction, the mixture is poured into an excess amount of water, the crystals obtained or the oily layer are separated by filtration or eistragir, oxidized with an organic solvent that is miscible with water, such as banzola, toluene, ethyl acetate, ether, and so on.

Example 1. K-3,4-H1N1HLOROPHENY-O-1methyl 5- / g-chloro: benzyl, goak | p | bonate.

In a solution of 5.6 g (0.1 mol) of 1-hydroxy oxide or 50 ml of methanol, 23.6 g (0.1 mol) of N-3.4 dichlorophenyl-O-methylthiO | | Carbonate is dissolved at room temperature. At this solution, about cayl, m is added at C 16.1 g (0.1 mol) -lorbenzyl: chloride and the resulting mixture is stirred for 2 hours. Then the reaction mixture is poured into 500 ml of water, the oil layer is extracted with ethyl acetate and washed once with water. The extract is then dried over sodium-free sulfate, the solvent is distilled off. L (33 g of an oily substance is obtained. This is an extensive substance is mixed with 50 ml of n-Haxane, the mixture is stirred at 1 dl., And temperature is obtained. Needle crystals are obtained. They are filtered, 31.4 g of 1x1-3,4-dichloro-O-methyl-3-p-chlorobenzylimino-thiocarbonate, with a high flow rate of 1 87%, are dried and agitated.

PREAMETE OF THE INVENTION

The method of obtaining imidocarbonate derivatives of the general formula

YR,

.

Sr,

where Y is oxygen, or sulfur.

Ar is an aromatic radical, which is not substituted or substituted by halogen or alkyl; a pyridine ring unsubstituted or substituted by halogeno M or nivalent alkyl with

the number of overhangs from I to 3;

RI is alkyl, unsubstituted or substituted by oxygru / I1Poi or al1 oxoxycarbonyl group; alkenyl, al1KI | Nile, araldyl, aromatic ring, "eschea or substituted

1-4 halogen atoms, 1-4 alkyl, or nitro group; phenoxyalkyl substituted with halides or lower alkyl;

RS is alkyl, for / messenger omsigroup or alkoxycarbonyl group; alkenyl, adduct; Il, aralkyl, aromatic ring, -substituted or substituted with 1–4 halogen atoms, 1–4 alkyl, and tropic or lower alkyl, m, c, / when Ar is an un-displaced benzene ring, Ri and R2 is aralkyl radicals, at least one of which has a substituent, characterized in that the thio.carbamine or dithiocarbamic acid esters of the general formula

Ag-NH-C-Y-Rb i S

where Ar, R and Y have the indicated meanings. Expose | Interaction with organic halides of the general formula

R2-X

where R2 Igmete specified values, X is a halogen atom, with the subsequent selection of the target product by known methods.