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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1066199Generated: November 1, 2026

Diglyme → 1-[2,6-Dichloro4-(4-trifluoromethylphenyl)phenyl]-3-cyano-4-trifluoromethylthio-5-aminopyrazole

https://huagongshe.com/reaction/1066199

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiglymeHCID 8150—
ReactantPotassium CarbonateHCID 11430—
Reactant4-(Trifluoromethyl)phenylboronic acidHCID 2734389—
ReactantHCID 86756989HCID 86756989—
CatalystTris(dibenzylideneacetone) dipalladiumHCID 9832798—
SolventWaterHCID 962—
Product1-[2,6-Dichloro4-(4-trifluoromethylphenyl)phenyl]-3-cyano-4-trifluoromethylthio-5-aminopyrazoleHCID 1543081766.4%

Reaction Conditions

Temperature20 °C

Reaction Steps

A mixture of 6 g of 5-amiino-3-cyano-1-(2,6-dichloro-4-bromophenyl)-4-trifluoromethylthiopyrazole (prepared according to procedures reported in U.S. Pat. No. 5,232,940), 4-trifluoromethylphenylboronic acid (5.3 g), K2CO3 (5.8 g), tris-(dibenzylidene acetone) dipalladium (0.6 g) and diglyme was heated at 130° C. for 25 hours. After cooling to 20° C., the mixture was poured into water and extracted with diethyl ether. The ether solutions were combined, dried, filtered and the filtrate concentrated and purified by chromatography. The desired product as a solid (3.9 g, mp 181-184° C.) was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06242475B1
Source datasetuspto-grants-2001_06
ORD IDord-ec6b699d5a9f4790b71052e7506a4beb
Source noteuspto-grants-2001_06