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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 532535Generated: October 26, 2026

Acetic Acid → 6-(4-Bromo-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

https://huagongshe.com/reaction/532535

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantHydrazine hydrate (1:1)HCID 24654—
Reactant5-(4-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-oneHCID 86699194—
SolventEthanolHCID 702—
Product6-(4-Bromo-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentaleneHCID 7174825297%

Reaction Conditions

Temperature25 °C

Reaction Steps

5-(4-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (8.0 g, 25 mmol), hydrazine monohydrate (4.8 mL, 150 mmol), glacial acetic acid (1.8 mL) and ethanol (45 mL) was heated at 100° C. under nitrogen for 4 hr. The mixture was cooled to 25° C. and concentrated under reduced pressure to give a solid which was recrystallized from ethanol to provide the corresponding 6-(4-Bromo-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (7.6 g, 24.2 mmol) as white solid in 97% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08853207B2
Source datasetuspto-grants-2014_10
ORD IDord-1fb2ec85110040048c3eadc934c8c69d
Source noteuspto-grants-2014_10