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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1024606Generated: October 29, 2026

Water → 5-(4-Bromo-phenyl)-6-(4-chloro-phenyl)-3-(3-methanesulfonyl-phenyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one

https://huagongshe.com/reaction/1024606

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant4-bromo-N-(4-chloro-phenyl)-benzimidoyl chlorideHCID 57898171—
Reactant5-amino-1-(3-methanesulfonyl-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl esterHCID 57899375—
CatalystTitanium TetrachlorideHCID 24193—
SolventDichloromethaneHCID 6344—
Solvent1,1-DichloroethaneHCID 6365—
Product5-(4-Bromo-phenyl)-6-(4-chloro-phenyl)-3-(3-methanesulfonyl-phenyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-oneHCID 57899411—

Reaction Conditions

Temperature150 °C

Reaction Steps

A mixture of 5-amino-1-(3-methanesulfonyl-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (310 mg, 1 mmol), 4-bromo-N-(4-chloro-phenyl)-benzimidoyl chloride (1.2 mmol) and TiCl4 (2 mmol) in anhydrous dichloroethane (5 mL) is heated to 150° C. for 14 h. After cooling down to room temperature, the mixture is diluted with CH2Cl2 (20 mL) and treated with water (30 mL). The solid is collected by filtration and washed with MeOH (5 ml) to provide the crude 5-(4-bromo-phenyl)-6-(4-chloro-phenyl)-3-(3-methanesulfonyl-phenyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one as yellow solid which is used for next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08722691B2
Source datasetuspto-grants-2014_05
ORD IDord-5bf6fc0e559442b3bc8000ea74818e68
Source noteuspto-grants-2014_05