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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 465135Generated: October 25, 2026

Sodium Carbonate → 1-{3-[(1,3-Benzothiazol-2-yl)methoxy]phenyl}pyrrolidine-2,5-dione

https://huagongshe.com/reaction/465135

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantCesium carbonateHCID 10796—
Reactant2-(Chloromethyl)benzothiazoleHCID 304978—
ReactantMethyl 4-(3-hydroxyanilino)-4-oxobutanoateHCID 13491817—
CatalystPotassium IodideHCID 4875—
SolventAcetoneHCID 180—
Product1-{3-[(1,3-Benzothiazol-2-yl)methoxy]phenyl}pyrrolidine-2,5-dioneHCID 1349181860.9%

Reaction Steps

A mixture of 4-[[3-(hydroxy)phenyl]amino]-4-oxobutanoic acid, methyl ester (1.45 g, 6.5 mmol), 2-chloromethylbenzothiazole (1.20 g, 6.5 mmol), cesium carbonate (1.0 g), sodium carbonate (0.7 g), potassium iodide (5 mg) and acetone (60 ml) is heated at reflux for 2 hours. The reaction is filtered through a pad of Celite and silica gel and the solvent is removed in vacuo. Recrystallization from acetone gives 1.34 g (56% yield) of product, m.p. 175°-176° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04550172
Source datasetuspto-grants-1985_10
ORD IDord-344a4a7e534e487d9fdbceb644f876a5
Source noteuspto-grants-1985_10