Ways to obtain 4,6-disubstituted 2-isocyanatobenzene and their use as intermediate products for the synthesis of biologically active substances

 

The invention relates to an improved process for the preparation of compounds of formula (I), where each of the residues X and Y independently of one another denotes hydrogen, halogen, (C1-C4)-alkyl, (C1-C4)-alkoxygroup or (C1-C4)-allylthiourea, each of the last three residues is unsubstituted or substituted by one or more residues from the group comprising halogen, (C1-C4)-alkoxygroup or (C1-C4)-allylthiourea, means or di[(C1-C4)alkyl]-amino, (C3-C6-cycloalkyl, (C3-C5)-alkenyl, (C3-C5)-quinil, (C3-C5)-alkenylacyl or (C3-C5)-alkyloxy, in which the compound of formula (II) or salts thereof, where X and Y are specified in the formula (I) values are subjected to interaction with 1-6 moles of phosgene per 1 mol of the compounds of formula (II) in the presence of 2-3,5 molar equivalents of an organic aminoaniline per mole of the compounds of formula (II) and in the presence of an aprotic organic solvent at the reaction temperature in the range from -30 to +60oC. the Invention also relates to an improved process for the preparation of compounds of formula (III) vzaimodejstvuyut to simplify the process, and to improve the yields and/or purity of the target product. 2 S. and 9 C.p. f-crystals.

Description text in facsimile form (see graphic part)n

Claims

1. The method of obtaining compounds of formula (I)

where each of the residues X and Y independently of one another denotes hydrogen, halogen, (C1-C4)-alkyl, (C1-C4)-alkoxygroup or (C1-C4)-allylthiourea, each of the last three residues is unsubstituted or substituted by one or more residues from the group comprising halogen, (C1-C4)-alkoxygroup or (C1-C4)-allylthiourea means or di[(C1-C4)alkyl]-amino, (C3-C6-cycloalkyl, (C3-C5)-alkenyl, (C3-C5)-quinil, (C3-C5)-alkenylacyl or (C3-C5)-alkyloxy, characterized in that the compound of formula (II) or its salt

where X and Y are specified in the formula (I) values are subjected to interaction with 1-6 moles of phosgene 1 moenia formula (II) and in the presence of an aprotic organic solvent at the reaction temperature in the range from -30 to +60To obtain the compounds of formula (I).

2. The method according to p. 1, characterized in that X and Y mean pairwise methyl/methyl, methyl/methoxy group, a chloro/methyl, chlorine or methoxy group or a methoxy group or methoxy group.

3. The method according to p. 1 or 2, characterized in that the interaction is carried out in the presence of 2-3 molar equivalents of base per 1 mol exposed to the interaction of the compounds of formula (II).

4. The method according to any of paragraphs.1-3, characterized in that the compound of formula (II) used as the base.

5. The method according to any of paragraphs.1-4, characterized in that use 1-3 molar equivalents of phosgene per mole at the interaction of the compounds of formula (II).

6. The method according to p. 5, characterized in that use 1.5 to 2 molar equivalent of phosgene per mole at the interaction of the compounds of formula (II).

7. The method according to any of paragraphs.1-6, characterized in that the used solvent from the group of aliphatic and aromatic hydrocarbons, halogenated aliphatic and aromatic hydrocarbons, cyclic or acyclic ethers, sulfones, esters of carboxylic acids, esters of carbonic acid and a mixture of several of the aforementioned solvents.

8. SPO is the slot with 1-4 carbon atoms and aliphatic alcohols with 1-10 carbon atoms.

9. The method of obtaining compounds of formula (III)

where X and Y have the meanings indicated in the formula (I), A denotes a hydrogen or a cation, for example, a cation of an alkali metal, Q means the residue of formula R*-Z-, where Z denotes the divalent group of formula-O-, -S-, -NR-, -CO-NR-, -CS-NR-, -SO2-, -SO2-NR-, -SO - or-SO2-NR-SO2-, where R is hydrogen or any of the above for R* residues,

R* means the residue from the group comprising alkyl, alkenyl, quinil, cycloalkyl, cycloalkenyl, alkoxygroup, aryl or heteroaryl, unsubstituted or substituted residues selected from the group comprising halogen, alkyl, haloalkyl, alkoxygroup, haloalkoxy, allylthiourea, a nitrogroup, cyano, asiagraph, alkoxycarbonyl, alkylsulphonyl, formyl, mono - and dialkylaminoalkyl, mono - and dialkylaminoalkyl, allmenalp, mono - and dialkylamino, alkylsulfonyl, haloalkylthio, alkylsulfonyl, haloalkylthio, the interaction of the corresponding compounds of formula (I) obtained by the method according to PP.1-8, with a nucleophilic compound of the formula (IV)

A-Q (IV)

where a and Q have the above significance.

10. The method according to p. 9, characterized in that compounds of the formula (III) pumice fact, the compounds of formula (III) are herbicide by the sulfonylureas.

 

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< / BR>
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< / BR>
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< / BR>
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