Process for manufacturing benzoxazinones

Patent metadata

Field	Value
Publication number	US-9518045-B2
Application number	US-201314421351-A
Country	US
Kind code	B2
Filing date	Aug 9, 2013
Priority date	Aug 17, 2012
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

The present invention relates to a process for manufacturing benzoxazinones of formula (I),

wherein the variables are defined according to the description,

by reacting carbamates of formula (II) are reacted with carbamat-benzoxazinones of formula (III) in the presence of a base.

First claim

The invention claimed is:

1. A process for manufacturing a compound of formula (I),

wherein
R 1 is H, halogen or C 1 -C 6 -alkyl;
R 2 is H, halogen or C 1 -C 6 -alkyl;
R 3 is H, halogen or C 1 -C 6 -alkyl;
R 4 is H, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy or C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl;
R 5 is H or C 1 -C 6 -alkyl;
R 6 is H or C 1 -C 6 -alkyl;
W is O or S; and
Z is O or S;

comprising reacting a compound of formula (II),

wherein R 7 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -cyanoalkyl, C 1 -C 6 -nitroalkyl, aryl, 5- or 6-membered heteroaryl or aryl-C 1 -C 6 -alkyl,
wherein the aryl or heteroaryl rings are unsubstituted, partially or fully halogenated, or substituted by one to five substituents selected from the group consisting of CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, OH, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, formyl, C 1 -C 6 -alkylcarbonyl, hydroxycarbonyl, and C 1 -C 6 -alkoxy carbonyl;

with a compound of formula (III),

wherein R 8 is C 1 -C 6 -haloalkyl, C 1 -C 6 -cyanoalkyl, C 1 -C 6 -nitroalkyl, aryl, 5- or 6-membered heteroaryl or aryl-C 1 -C 6 -alkyl,
wherein the aryl or heteroaryl rings are unsubstituted, partially or fully halogenated, or substituted by one to five substituents selected from the group consisting of CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, OH, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, formyl, C 1 -C 6 -alkylcarbonyl, hydroxycarbonyl, and C 1 -C 6 -alkoxycarbonyl;

in the presence of a base.

2. The process as claimed in claim 1 , wherein R 1 , R 2 and R 3 are halogen.

3. The process as claimed in claim 1 , wherein W is O and Z is S.

4. The process as claimed in claim 1 , wherein R 7 is C 1 -C 6 -alkyl or aryl, wherein the aryl ring is unsubstituted, partially or fully halogenated, or substituted by one to five substituents selected from the group consisting of CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, OH, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy.

5. The process as claimed in claim 1 , wherein R 7 is C 1 -C 6 -alkyl.

6. The process as claimed in claim 1 , wherein R 8 is aryl, wherein the aryl ring is unsubstituted, partially or fully halogenated, or substituted by one to five substituents selected from the group consisting of CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, OH, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy.

7. The process as claimed in claim 1 , wherein R 8 is aryl, wherein the aryl ring is unsubstituted.

8. The process as claimed in claim 1 , wherein R 7 and R 8 are aryl, wherein the aryl ring is unsubstituted, partially or fully halogenated, or substituted by one to five substituents selected from the group consisting of CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, OH, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy.

9. The process as claimed in claim 1 , wherein R 7 and R 8 are aryl, wherein the aryl ring is unsubstituted.

10. The process as claimed in claim 1 , wherein the compound R 7 O—H formed in the course of the reaction is partly or completely distilled out of the reaction mixture.

11. The process as claimed in claim 1 , wherein the compound of formula (II) is prepared by reacting a compound of formula (IV),

with a compound of formula (V)

in the presence of a base.

12. The process as claimed in claim 1 , wherein the compound of formula (III) is prepared by reacting a compound of formula (VI),

with a compound of formula (VII)

13. The process as claimed in claim 1 , wherein the compound of formula (II) is prepared by reacting a compound of formula (IV),

with a compound of formula (V)

in the presence of a base; and
the compound of formula (III) is prepared by reacting a compound of formula (VI),

with a compound of formula (VII)

14. A process for preparing the compound of formula (I)

wherein
R 1 is H or halogen;
R 2 is halogen;
R 3 is H or halogen;
R 4 is H, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy or C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl;
W is O or S,
R 6 is H or C 1 -C 6 -alkyl;
R 5 is H or C 1 -C 6 -alkyl;
and
Z is O or S;

comprising preparing a compound of formula (III)

by reacting a compound of formula (VI),

with a compound of formula (VII)

wherein
R 8 is phenyl, which is unsubstituted, partially or fully halogenated, or substituted by one to five substituents selected from the group consisting of CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, OH, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, formyl, C 1 -C 6 -alkylcarbonyl, hydroxycarbonyl, and C 1 -C 6 -alkoxycarbonyl;

to obtain a compound of formula (III);
reacting the compound of formula (III) with a compound formula (II)

wherein
R 7 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -cyanoalkyl, C 1 -C 6 -nitroalkyl, aryl, 5- or 6-membered heteroaryl or aryl-C 1 -C 6 -alkyl,
wherein the aryl or heteroaryl rings are unsubstituted, partially or fully halogenated, or substituted by one to five substituents selected from the group consisting of CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, OH, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, formyl, C 1 -C 6 -alkylcarbonyl, hydroxycarbonyl, and C 1 -C 6 -alkoxycarbonyl;

in the presence of a base to obtain a compound of formula (I).

Assignees

• Basf Se

Inventors

• Dochnahl Maximilian
• Goetz Roland
• Gebhardt Joachim
• Vogelbacher Uwe Josef
• Frassetto Timo
• Rack Michael
• Maywald Volker
• Wolf Bernd

Classifications

• C07D413/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D265/36

  condensed with one six-membered ring · CPC title

• C07C335/28

  Y being a hetero atom, e.g. thiobiuret · CPC title