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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 430656Generated: October 25, 2026

Phthalimide → 5-(4-Nitrophenyl)-8-(phthalimidomethyl)-9H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine

https://huagongshe.com/reaction/430656

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhthalimideHCID 6809—
ReactantTriphenylphosphineHCID 11776—
Reactantethyl N-ethoxycarbonyliminocarbamateHCID 220568—
Reactant8-Hydroxymethyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepineHCID 18183191—
SolventTetrahydrofuranHCID 8028—
Product5-(4-Nitrophenyl)-8-(phthalimidomethyl)-9H-1,3-dioxolo[4,5-h][2,3]-benzodiazepineHCID 18183124—

Reaction Steps

A solution of 1.25 ml (8.05 mmol) of diethyl azodicarboxylate in 7 ml of THF is added in drops to a stirred solution of 2.60 g (7.66 mmol) of 8-hydroxymethyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine (starting compound III.), 2.11 g (8.05 mmol) of triphenylphosphine and 1.18 g (8.05 mmol) of phthalimide in 130 ml of dry THF at room temperature. The mixture is stirred for 24 hours at this temperature. Then, the precipitated product is suctioned off and washed with ethanol. 2.87 g (80%) of the title compound, which can be further processed without further purification, is obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06323197B1
Source datasetuspto-grants-2001_11
ORD IDord-6429d3d3bc204717b1ac0026f57232c5
Source noteuspto-grants-2001_11