# US 7,608,736 B2 · Process for preparing acylsulfamoylbenzamides

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- Number: US 7,608,736 B2
- Document ID: US7608736B2
- Status: Granted
- Kind: B2
- Application number: 10/874,966
- Filed: 2004-06-23
- Published: 2005-01-06
- Granted: 2009-10-27
- Earliest claimed: 2004-06-23
- Assignees: Bayer CropScience AG
- Inventors: Sergiy Pazenok; Mark James Ford; Günter Schlegel
- Web page: https://patentgrep.com/patent/US7608736B2

## CPC

- C07C 303/40: by reactions not involving the formation of sulfonamide groups
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The invention relates to a process for the preparation of a compound of formula (I): Which comprises reaction of a compound of formula (II) with a compound of the formula (III) in the presence of a chlorinating agent, followed by reaction of the resultant compound of the formula (IV) with a compound of formula (V) in the presence of a base: wherein the various symbols are as defined in claim 1.

## Claims

### Claim 1

A process for the preparation of a compound of formula (I):
wherein:
R1 is hydrogen, —(CH2)p-heterocyclyl or a hydrocarbon radical, where the two last-mentioned radicals are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, cyano and nitro;
R2 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, where the five last-mentioned radicals are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkoxy and (C1-C4)-alkylthio; or R1 and R2 together with the linking nitrogen atom form a 3- to 8-membered saturated or unsaturated ring;
R3 and R5 are each independently halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, S(O)q—(C1-C6)-alkyl, (C1-C6)-alkylcarbonyl, —CO-aryl, cyano or nitro; or two adjacent R5 groups form a —O—CH2CH2— moiety;
R4 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl;
n is an integer from 0 to 4;
m is an integer from 0 to 5;
p is 0 or 1; and
q is 0, 1 or 2; or a salt thereof;
which process comprises the reaction of a compound of formula (II):
wherein R3, R4 and n are as defined in formula (I), with a compound of formula (III):
wherein R5 and m are as defined in formula (I) and Y is OH or Cl, in the presence of a chlorinating agent, to give a compound of formula (IV):
wherein R3, R4, R5, m and n are as defined in formula (I), followed by the reaction of the resultant compound of formula (IV) with a compound of formula (V):
R1R2NH (V)
wherein R1 and R2 are as defined in formula (I), in the presence of a base.

### Claim 2 (depends on 1)

A process as claimed in claim 1 wherein the chlorinating agent is thionyl chloride.

### Claim 3 (depends on 1)

A process as claimed in claim 1 wherein the amount of chlorinating agent used is, when Y is OH from 1 to 2 molar equivalents per equivalents of (II) and (IIIa), or when Y is Cl from 1 to 2 molar equivalents per equivalent of (II).

### Claim 4 (depends on 1)

A process as claimed in claim 1 wherein the solvent used in the reaction of the compound of formula (II) with the compound of formula (III) is chlorobenzene.

### Claim 5 (depends on 3)

A process as claimed in claim 3 wherein the chlorinating agent is thionyl chloride.

### Claim 6 (depends on 2)

A process as claimed in claim 2 wherein the solvent used in the reaction of the compound of formula (II) with the compound of formula (III) is chlorobenzene.

### Claim 7 (depends on 6)

A process as claimed in claim 6 wherein the amount of chlorinating agent used is, when Y is OH from 1 to 2 molar equivalents of (II) and (IIIa) or when Y is Cl from 1 to 2 molar equivalents per equivalent of (II).

### Claim 8 (depends on 1)

A process as claimed in claim 1 wherein:
R1 is hydrogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl;
R2 and R4 are each hydrogen;
R5 is (C1-C6)-alkoxy;
n is 0;
m is 0 or 1;
and the sulfamoyl group is located para to the CONR1R2 moiety in the phenyl ring.

### Claim 9 (depends on 7)

A process as claimed in claim 7 wherein:
R1 is hydrogen or (C1-C6)-alkyl;
R2 is hydrogen or (C1-C6)-alkyl;
R4 is hydrogen;
R5 is (C1-C6)-alkoxy;
n is 0;
m is 0 or 1;
and the sulfamoyl group is located para to the CONR1R2 moiety in the phenyl ring.