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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 660712Generated: October 30, 2026

Sodium Carbonate → 5-[2-benzyloxy-4-((E)-hex-1-enyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

https://huagongshe.com/reaction/660712

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantB-(1E)-1-Hexenylboronic acidHCID 5326225—
Reactant5-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-oneHCID 68838643—
Solvent1,2-DimethoxyethaneHCID 8071—
Product5-[2-benzyloxy-4-((E)-hex-1-enyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-oneHCID 68839290—

Reaction Conditions

Temperature110 °C

Reaction Steps

A mixture of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (200 mg, 0.45 mmol), trans-1-hexen-1-ylboronic acid (77 mg, 0.676 mmol), resin-bound PPh3Pd (692 mg, loading 0.13 mmol/g) and aqueous Na2CO3 (0.9 mL of a 2M solution) in DME (3 mL) is placed in a microwave vial and heated at 110° C. for 30 min. The mixture is filtered, diluted with EtOAc and washed with 1N HCl. The organic phase is dried over magnesium sulfate and the solvent removed under reduced pressure. The residue is purified by preparative HPLC to give the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08084448B2
Source datasetuspto-grants-2011_12
ORD IDord-105f284162aa4b98b7266577f6f8db05
Source noteuspto-grants-2011_12