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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1626352Generated: October 26, 2026

Benzoic Acid → (Z)-tert-Butyl 4-((6-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate

https://huagongshe.com/reaction/1626352

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzoic AcidHCID 243—
ReactantThiazolidinedioneHCID 5437—
ReactantPiperidineHCID 8082—
Reactanttert-Butyl 4-((6-(4-formylphenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylateHCID 86697014—
SolventTolueneHCID 1140—
Product(Z)-tert-Butyl 4-((6-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylateHCID 5696050766.3%

Reaction Conditions

Temperature30 °C

Reaction Steps

To a solution of tert-butyl 4-((6-(4-formylphenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate (950 mg, 0.002298 mole), thiazolidine-2,4-dione (241 mg, 0.00206 mole) and benzoic acid (0.0364 mg, 0.000298 mole) in toluene (30 ml), piperidine (0.033 ml, 0.00344 mole) was added and reaction mixture was refluxed for 7 hours using Dean-Stark apparatus. Then reaction mixture was cooled to 30° C. and solid product was filtered, washed with ice cold toluene and dried to yield 700 mg white solid product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08785463B2
Source datasetuspto-grants-2014_07
ORD IDord-6246c129ce9c4a2b9e5f09bd22435c91
Source noteuspto-grants-2014_07