Method for producing hydrazine compound,and production intermediates of hydrazine compound and methods of producing the intermediates
AssigneeSumitomo Chemical Company, Limited
InventorsTaro Hirose, Kengo Kanematsu
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Abstract
Provided are a novel method for producing a hydrazine compound useful as an insecticidal compound, and production intermediates which can be suitably used for the production method and methods for producing the intermediates. As the production intermediates, a specific isocyanate compound and an organomagnesium compound represented by the following general formula (IV) are provided. The organomagnesium compound can be synthesized from a corresponding dibromo compound.
Claims7
A method for producing a hydrazine compound, comprising a step of:
- reacting an isocyanate compound represented by the following general formula (II):
- wherein R1 and R2 each independently represent an alkyl group having 1 to 6 carbons;
- R3 represents an alkyl group having 1 to 6 carbons, an alkoxyalkyl group having 3 to 6 carbons, an alkenyl group having 3 to 6 carbons or an alkynyl group having 3 to 6 carbons;
- R4 represents halogen, an alkyl group having 1 to 6 carbons or a perfluoroalkyl group having 1 to 6 carbons;
- and R5 represents hydrogen, halogen, a cyano group, an alkyl group having 1 to 6 carbons or a perfluoroalkyl group having 1 to 6 carbons,
- with an organometallic compound represented by the following general formula (III):
- wherein R6 represents hydrogen, halogen, a cyano group, an alkyl group having 1 to 6 carbons optionally substituted with halogen, an alkoxy group having 1 to 6 carbons optionally substituted with halogen, an alkylthio group having 1 to 6 carbons optionally substituted with halogen, an alkylsulfinyl group having 1 to 6 carbons optionally substituted with halogen or an alkylsulfonyl group having 1 to 6 carbons optionally substituted with halogen;
- R7 represents halogen or an alkyl group having 1 to 6 carbons optionally substituted with halogen;
- M represents Li, MgX or ZnX;
- and X represents chlorine, bromine or iodine,
- the hydrazine compound being represented by the following general formula (I):
- wherein R1 to R7 are the same as described above.
An isocyanate compound represented by the following general formula (II):
- wherein R1 and R2 each independently represent an alkyl group having 1 to 6 carbons;
- R3 represents an alkyl group having 1 to 6 carbons, an alkoxyalkyl group having 3 to 6 carbons, an alkenyl group having 3 to 6 carbons or an alkynyl group having 3 to 6 carbons;
- R4 represents halogen, an alkyl group having 1 to 6 carbons or a perfluoroalkyl group having 1 to 6 carbons;
- and R5 represents hydrogen, halogen, a cyano group, an alkyl group having 1 to 6 carbons or a perfluoroalkyl group having 1 to 6 carbons.
An organomagnesium compound represented by the following general formula (IV):
- wherein X represents chlorine, bromine or iodine.
A method for producing an organomagnesium compound, comprising a step of:
- reacting a dibromo compound represented by the following formula (V):
- with a Grignard compound represented by the following general formula (VI):
- R—MgX (VI)
- wherein R represents an alkyl group having 1 to 6 carbons or a vinyl group;
- and
- X represents chlorine, bromine or iodine,
- the organomagnesium compound being represented by the general formula (IV):
- wherein X represents chlorine, bromine or iodine.
A dibromo compound represented by the following formula (V):
A method for producing a formyl compound, comprising a step of:
- reacting an organomagnesium compound represented by the following general formula (IV):
- wherein X represents chlorine, bromine or iodine,
- with a compound represented by the following general formula (VII):
- HC(═O)-Q (VII)
- wherein Q represents an amino group substituted with two alkyl groups each having 1 to 6 carbons or an alkoxy group having 1 to 3 carbons,
- the formyl compound being represented by the following formula (VIII):
Dependencies are inferred from the claim text.