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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 56202Generated: October 27, 2026

But-1-ene-1,3-dione → N-(3-bromo-4-(dihexylamino)phenyl)-3-oxobutanamide

https://huagongshe.com/reaction/56202

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBut-1-ene-1,3-dioneHCID 12642904—
Reactant2-bromo-N1,N1-dihexylbenzene-1,4-diamineHCID 101043124—
SolventEthyl AcetateHCID 8857—
ProductN-(3-bromo-4-(dihexylamino)phenyl)-3-oxobutanamideHCID 9002427994%

Reaction Conditions

Temperature80 °C

Reaction Steps

To a solution of 2-bromo-N1,N1-dihexylbenzene-1,4-diamine (4.40 g, 12.4 mmol) in EtOAc (120 mL) was added acetyl ketene (1.57 g, 18.7 mmol), and the mixture was stirred at 80° C. overnight. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1) to give the title compound as colorless oil (5.10 g, 94%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09434695B2
Source datasetuspto-grants-2016_09
ORD IDord-b5e6fbb37cf14b928abc4e6fac0d5253
Source noteuspto-grants-2016_09