Process for preparing 4[[(benzoyl)amino]sulphonyl]benzoyl chlorides and preparation of acylsulphamoylbenzamides

Patent metadata

Field	Value
Publication number	US-9725409-B2
Application number	US-201415024352-A
Country	US
Kind code	B2
Filing date	Oct 7, 2014
Priority date	Oct 10, 2013
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

Process for preparing 4-[[(benzoyl)amino]sulphonyl]benzoyl chlorides of the formula (II).

First claim

The invention claimed is:

1. A process for preparing 4-[[(benzoyl)amino]sulphonyl]benzoyl chloride of formula (II)

in which
R 1a to R 1e and R 2a to R 2d are each independently selected from the group consisting of hydrogen, halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 3 -C 7 -cycloalkoxy), (C 3 -C 7 )-cycloalkyl, (C 1 -C 6 )-alkylthio, (C 3 -C 7 )-cycloalkylthio, S(O) q —(C 1 -C 6 )-alkyl with q=0, 1 or 2, (C 1 -C 6 )-alkylcarbonyl, —CO-aryl, cyano and nitro, or in which any two adjacent R 1a to R 1e radicals form a —O—CH 2 CH 2 — radical, proceeding from a compound of the formula (III)

in which
R 1a to R 1e are each as defined above, and
a compound of formula (IV)

in which
R 2a to R 2d are each as defined above, by reacting a compound of formula (III) and a compound of formula (IV)
in an aprotic polar solvent, or
in an aprotic polar solvent composition comprising at least one aprotic polar solvent.

2. A process for preparing a compound of the formula (II) according to claim 1 , wherein R 1a to R 1e and R 2a to R 2d are each independently selected from the group consisting of
hydrogen, fluorine, chlorine, bromine,
(C 1 -C 6 )-alkyl, where the alkyl radical is branched or unbranched and is unsubstituted or substituted by one or more substituents selected from the group consisting of (C 1 -C 4 )-alkoxy and (C 3 -C 7 )-cycloalkyl,
(C 1 -C 6 )-haloalkyl, where the alkyl radical is unsubstituted or substituted by one or more substituents selected from the group consisting of fluorine, chlorine, bromine and iodine,
(C 3 -C 7 )-cycloalkyl, where the cycloalkyl radical is unsubstituted or substituted by one or more substituents selected from the group consisting of (C 1 -C 4 )-alkyl, (C 3 -C 7 )-cycloalkyl, and (C 1 -C 4 )-alkoxy,
(C 1 -C 6 )-alkoxy, where the alkoxy radical is branched or unbranched and is unsubstituted or substituted by one or more substituents selected from the group consisting of (C 1 -C 4 )-alkoxy and (C 3 -C 7 )-cycloalkyl,
(C 3 -C 7 )-cycloalkoxy, where the cycloalkoxy radical is unsubstituted or substituted by one or more substituents selected from the group consisting of (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy,
(C 1 -C 6 )-alkylthio, where the alkylthio radical is branched or unbranched and is unsubstituted or substituted by one or more substituents selected from the group consisting of (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy, and
(C 3 -C 7 )-cycloalkylthio, where the cycloalkylthio radical is unsubstituted or substituted by one or more substituents selected from the group consisting of (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy.

3. A process for preparing a compound of formula (II) according to claim 2 , wherein R 1a is an unsubstituted (C 1 -C 4 )-alkoxy radical, and R 1b to R 1e and R 2a to R 2d are each hydrogen.

4. A process for preparing a compound of formula (II) according to claim 3 , wherein R 1a is methoxy (—O—CH 3 ), and R 1b to R 1e and R 2a to R 2d are each hydrogen.

5. A process for preparing a compound of formula (II) according to claim 1 , wherein the aprotic polar solvent used includes open-chain ketones, cyclic ketones, esters, amides, nitriles or ethers, each of which are unsubstituted or substituted by one or more substituents selected from the group consisting of halogen and (C 1 -C 6 )alkyl.

6. A process for preparing a compound of formula (II) according to claim 5 , wherein the aprotic polar solvent has a molecular weight of less than 200.

7. A process for preparing a compound of formula (II) according to claim 1 , wherein the aprotic polar solvent is selected from the group consisting of cyclohexanone, methyl isobutyl ketone, diisobutyl ketone, ethyl acetate, propyl acetate, butyl acetate, isopropyl acetate, isobutyl acetate, ethyl propionate, ethyl butyrate, propyl propionate, isopropyl propionate, dialkylacetamide, cycloalkylacetamide, acetonitrile, propionitrile, butyronitrile, valeronitrile, methyl tert-butyl ether, tetrahydrofuran and methyltetrahydrofuran.

8. The process for preparing compounds of the formula (II) according to claim 6 , wherein the aprotic polar solvent is selected from the group consisting of esters of acetic acid and esters of propionic acid.

9. A process for preparing compounds of the formula (II) according to claim 7 , wherein the aprotic polar solvent is selected from the group consisting of isopropyl acetate, isobutyl acetate and ethyl propionate.

10. A process for preparing compounds of the formula (II) according to claim 7 , wherein the reactant of formula (III) and the reactant of formula (IV) an aprotic polar solvent composition comprising at least two aprotic polar solvents selected from the group consisting of isopropyl acetate, isobutyl acetate and ethyl propionate.

11. A process for preparing a compound of formula (II) according to claim 1 , wherein the process further comprises a chlorinating agent and wherein the chlorinating agent is thionyl chloride.

12. A process for preparing a compound of formula (II) according to claim 1 , wherein reaction of reactants is effected
within a temperature range from 20° C. to 90° C. and
within a pressure range from 0.1 to 10 bar.

13. A process for preparing a compound of formula (Ia)

in which
R 1a to R 1e and R 2a to R 2d are each independently selected from the group consisting of hydrogen, halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 3 -C 7 )-cycloalkyl, (C 1 -C 6 )-alkylthio, (C 3 -C 7 )-cycloalkylthio, S(O) q —(C 1 -C 6 )-alkyl with q=0, 1 or 2, (C 1 -C 6 )-alkylcarbonyl, —CO-aryl, cyano and nitro, or in which any two adjacent R 1a to R 1e radicals form a —O—CH 2 CH 2 — radical, and
R 3a is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 7 )-cycloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylthio, (C 3 -C 7 )-cycloalkylthio, and —CH 2 -heterocyclyl, where each of these is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, cyano and nitro, and
R 3b is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy, and —CH 2 -heterocyclyl,
where each of these is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C 1 -C 4 )-alkoxy and (C 1 -C 4 )-alkylthio, or
R 3a and R 3b together with the connecting nitrogen atom form a 3- to 8-membered saturated or unsaturated ring,
by reacting a compound of formula (II)

in which R 1a to R 1e and R 2a and R 2d are as defined above,
with an amine of the formula R 3a R 3b NH in which the R 3a and R 3b radicals are each as defined above, wherein the compound of the formula (II) is prepared by the process according to claim 1 , and wherein the compound of the formula (II) is charged for the reaction with the amine R 3a R 3b NH
without prior isola

Assignees

• Bayer Cropscience Ag

Inventors

• Farida Taraneh
• Stakemeier Hubertus
• Vermehren Jan

Classifications

• C07D303/40 Primary

  by ester radicals · CPC title

• C07C311/51

  Y being a hydrogen or a carbon atom · CPC title

• C07C303/40 Primary

  by reactions not involving the formation of sulfonamide groups · CPC title

• C07C303/36

  of amides of sulfonic acids · CPC title

• C07C303/44

  Separation; Purification · CPC title