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US 9,518,045 B2Granted
Process for manufacturing benzoxazinones
AssigneeBASF SE
InventorsMaximilian Dochnahl, Roland Goetz, Joachim Gebhardt, Uwe Josef Vogelbacher, Timo Frassetto, Michael Rack, Volker Maywald, Bernd Wolf
Life of this patent
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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.
Claims14
A process for manufacturing a compound of formula (I),
- wherein
- R1 is H, halogen or C1-C6-alkyl;
- R2 is H, halogen or C1-C6-alkyl;
- R3 is H, halogen or C1-C6-alkyl;
- R4 is H, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C1-C6-alkoxy or C3-C6-cycloalkyl-C1-C6-alkyl;
- R5 is H or C1-C6-alkyl;
- R6 is H or C1-C6-alkyl;
- W is O or S;
- and
- Z is O or S;
- comprising reacting a compound of formula (II),
- wherein R7 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C1-C6-nitroalkyl, aryl, 5- or 6-membered heteroaryl or aryl-C1-C6-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, NO2, C1-C6-alkyl, C1-C6-haloalkyl, OH, C1-C6-alkoxy, C1-C6-haloalkoxy, formyl, C1-C6-alkylcarbonyl, hydroxycarbonyl, and C1-C6-alkoxy carbonyl;
- with a compound of formula (III),
- wherein R8 is C1-C6-haloalkyl, C1-C6-cyanoalkyl, C1-C6-nitroalkyl, aryl, 5- or 6-membered heteroaryl or aryl-C1-C6-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, NO2, C1-C6-alkyl, C1-C6-haloalkyl, OH, C1-C6-alkoxy, C1-C6-haloalkoxy, formyl, C1-C6-alkylcarbonyl, hydroxycarbonyl, and C1-C6-alkoxycarbonyl;
- in the presence of a base.
14 more elements
A process for preparing the compound of formula (I)
- wherein
- R1 is H or halogen;
- R2 is halogen;
- R3 is H or halogen;
- R4 is H, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C1-C6-alkoxy or C3-C6-cycloalkyl-C1-C6-alkyl;
- W is O or S,
- R6 is H or C1-C6-alkyl;
- R5 is H or C1-C6-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
- R8 is phenyl, which is unsubstituted, partially or fully halogenated, or substituted by one to five substituents selected from the group consisting of CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, OH, C1-C6-alkoxy, C1-C6-haloalkoxy, formyl, C1-C6-alkylcarbonyl, hydroxycarbonyl, and C1-C6-alkoxycarbonyl;
- to obtain a compound of formula (III);
- reacting the compound of formula (III) with a compound formula (II)
- wherein
- R7 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C1-C6-nitroalkyl, aryl, 5- or 6-membered heteroaryl or aryl-C1-C6-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, NO2, C1-C6-alkyl, C1-C6-haloalkyl, OH, C1-C6-alkoxy, C1-C6-haloalkoxy, formyl, C1-C6-alkylcarbonyl, hydroxycarbonyl, and C1-C6-alkoxycarbonyl;
- in the presence of a base to obtain a compound of formula (I).
18 more elements
Dependencies are inferred from the claim text.