Thionyl Chloride → 4-bromo-N-(4-chloro-phenyl)-benzimidoyl chloride

Participants

Role	Name	HCID	Charge
Reactant	Thionyl Chloride	HCID 24386	—
Reactant	HCID 774372	HCID 774372	—
Reactant	6-(4-Bromo-phenyl)-5-(4-chloro-phenyl)-1-(3-methylsulfanyl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one	HCID 24781619	—
Solvent	Toluene	HCID 1140	—
Product	4-bromo-N-(4-chloro-phenyl)-benzimidoyl chloride	HCID 57898171	—

Reaction Conditions

Temperature	170 °C

Reaction Steps

4-Bromo-N-(4-chloro-phenyl)-benzimidoyl chloride is prepared by heating 4-bromo-N-(4-chloro-phenyl)-benzamide (16.5 g, 53.0 mmol) and thionyl chloride (140 mL) for 1 h. The clear solution is concentrated and the residue obtained is coevaporated with toluene (100 mL). Then 5-amino-1-(3-methylsulfanyl-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester (1, 9.8 g, 35.33 mmol) is added and the resulting mixture is heated to 170° C. with out solvent for 6 h. The crude product obtained is purified by column chromatography (6).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08722691B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-6d535525cfcc4a3e846fdbe72fbfd2e7
Source note	uspto-grants-2014_05