Carbamates

Patent metadata

Field	Value
Publication number	US-9409894-B2
Application number	US-201314421321-A
Country	US
Kind code	B2
Filing date	Jul 29, 2013
Priority date	Aug 17, 2012
Publication date	Aug 9, 2016
Grant date	Aug 9, 2016

Abstract

The present invention relates to carbamates of formula (I),

wherein the variables are defined according to the description,
as well as to a process for manufacturing carbamates of formula (I), and to the use of carbamates of formula (I) in manufacturing benzoxazinones of formula (VII).

First claim

The invention claimed is:

1. A compound of formula (I),

wherein
R 1 is H or C 1 -C 6 -alkyl;
R 2 is methyl;
R 3 is methyl, 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;

and
Z is S.

2. The compound of claim 1 , wherein R 3 is methyl or aryl, wherein the aryl ring is unsubstituted or substituted by one halogen atom or one C 1 -C 6 -alkyl group.

3. The compound of claim 1 , wherein R 1 is methyl.

4. The compound of claim 1 , wherein R 1 and R 3 are both methyl.

5. The compound of claim 1 , wherein R 1 is methyl and R 3 is phenyl.

6. A process for the preparation of the compound of formula (I) as claimed in claim 1 wherein a compound of formula (II),

is reacted with the compound of formula (III)

in the presence of a base.

7. A process for preparing a compound of formula (II) comprising
a) reacting a compound of formula (IV)
Z═C═N—R 1   (IV)

wherein

R 1 is H or C 1 -C 6 -alkyl; and
Z is S
With a compound of formula (V)
H 2 N—R 2   (V)

wherein R 2 is methyl.

8. The process as claimed in claim 7 , wherein the compound of formula (II) is not isolated, and the reaction mixture obtained in step a) is directly used in the reaction to give carbamates of formula (I).

Assignees

• Basf Se

Inventors

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

Classifications

• C07C335/28

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

• C07D265/36

  condensed with one six-membered ring · CPC title

• C07C275/60

  Y being an oxygen atom, e.g. allophanic acids · CPC title

• C07D413/04 Primary

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