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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 25334Generated: October 26, 2026

Benzenesulfonyl chloride → 2-Benzenesulfonyl-2,9-dihydro-6-oxa-2-azabenzo[cd]azulen-8-one Ethylene Ketal

https://huagongshe.com/reaction/25334

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzenesulfonyl chlorideHCID 7369—
ReactantSodium hydrideHCID 24758—
Reactant2,9-Dihydro-6-oxa-2-azabenzo[cd]azulen-8-one Ethylene KetalHCID 86590588—
SolventDimethylformamideHCID 6228—
SolventChloroform hexaneHCID 21585165—
Product2-Benzenesulfonyl-2,9-dihydro-6-oxa-2-azabenzo[cd]azulen-8-one Ethylene KetalHCID 8659058769%

Reaction Conditions

Temperature60 °C

Reaction Steps

60% Sodium hydride 33 mg was added to a solution of compound (33) in dry dimethylformamide 2 ml with cooling in ice and the mixture was stirred for 10 min. Then, benzenesulfonyl chloride 152 mg was added. The mixture was heated at 60° C. for 14 h. Ice-water was added to the reaction mixtures, which was extracted with ethyl acetate. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was choromatographed on aluminum oxide in chloroform:hexane (1:1) to give the titled compound (34) as a pale yellow oil, 187 mg. Yield 69%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06858640B2
Source datasetuspto-grants-2005_02
ORD IDord-ba1684af748a480b843e644ec5830dbc
Source noteuspto-grants-2005_02