Water → n-[4-Chloro-2-(n-methylhydrazinocarbonyl)-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1h-pyrazole-5-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Methylhydrazine	HCID 6061	—
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	6-chloro-2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-8-methylbenzo[d][1,3]oxazin-4-one	HCID 23150351	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	n-[4-Chloro-2-(n-methylhydrazinocarbonyl)-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1h-pyrazole-5-carboxamide	HCID 66854233	82.3%

Reaction Steps

A mixture of 0.44 g of 6-chloro-2-[1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazine-4-one, 0.05 g of methylhydrazine and 10 ml of tetrahydrofuran was stirred at room temperature for 2 hours. After the reaction mixture was mixed with water and ethyl acetate, layers were separated. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.40 g of N-[4-chloro-2-(N-methylhydrazinocarbonyl)-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazole-5-carboxamide of the formula:

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07968573B2
Source dataset	uspto-grants-2011_06
ORD ID	ord-79ee6dd105cd42a4ae7db9afc963fb7b
Source note	uspto-grants-2011_06