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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 453111Generated: October 30, 2026

Water → 5-(4-Chloro-2-methoxyphenyl)-1,3,4-oxathiazol-2-one

https://huagongshe.com/reaction/453111

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant(Chlorothio)formyl chlorideHCID 75990—
ReactantHCID 19741766HCID 19741766—
SolventTolueneHCID 1140—
Product5-(4-Chloro-2-methoxyphenyl)-1,3,4-oxathiazol-2-oneHCID 5954952495.6%

Reaction Conditions

Temperature90 °C

Reaction Steps

To a solution of 4-chloro-2-methoxybenzamide (0.82 g, 4.42 mmol) in toluene (20 ml) was added chlorocarbonylsulfenyl chloride (0.73 ml, 8.84 mmol) under nitrogen atmosphere and the resulting reaction mixture was refluxed at 90° C. for 2 h. After the completion of the reaction (TLC monitoring) water was added followed by extraction with ether (3×50 ml). The combined organics was then sequentially washed with water, 10% NaHCO3 (aqueous solution) and finally again with water. The organic layer was then dried over anhydrous Na2SO4, filtered and concentrated to get desired product (1.03 g, 96% crude yield) that was carried forward as such without further purification. MS: 244.16 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08492414B2
Source datasetuspto-grants-2013_07
ORD IDord-67797e54e86642398735e9dd5561b00f
Source noteuspto-grants-2013_07