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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1460620Generated: November 2, 2026

Chlorosuccinimide → trans-4-[N-(2-chloro-3-oxo-cyclopent-1-enyl)amino]-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

https://huagongshe.com/reaction/1460620

Reaction equation

Participants

RoleNameHCIDCharge
ReactantChlorosuccinimideHCID 31398—
Reactanttrans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(3-oxo-1-cyclopent-1-enylamino)-2H-1-benzopyran-6-carbonitrileHCID 14301304—
SolventDichloromethaneHCID 6344—
Solvent1,4-DioxaneHCID 31275—
Producttrans-4-[N-(2-chloro-3-oxo-cyclopent-1-enyl)amino]-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrileHCID 14301326—

Reaction Steps

A solution of 150 mg of the title compound of example 5 in 5 ml of dichloromethan and 5 ml of dioxan is mixed with 77 mg of N-chloro-succinimide. After 50 minutes at room temperature the solution is poured on water and the organic components are extracted with dichloromethane/ethanol. Recristallisation of the raw product obtained after concentration yields white crystalls of the title compound having a m.p. of 288°-89° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05071871
Source datasetuspto-grants-1991_12
ORD IDord-413cec147b324d009e8e038997855d44
Source noteuspto-grants-1991_12