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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 27678Generated: October 26, 2026

Formamide → 2-((4-(Diethylamino)phenyl)azo)-5-nitrobenzonitrile

https://huagongshe.com/reaction/27678

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormamideHCID 713—
ReactantAcetic AnhydrideHCID 7918—
ReactantSodium AcetateHCID 517045—
Reactant2-Bromo-4-nitro-4'-(N,N-diethylamino)azobenzeneHCID 23341444—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
SolventButyl AcetateHCID 31272—
Product2-((4-(Diethylamino)phenyl)azo)-5-nitrobenzonitrileHCID 301582275%

Reaction Conditions

Temperature110 °C

Reaction Steps

2-Bromo-4-nitro-4'-(N,N-diethylamino)azobenzene (1.9 parts), copper (I) iodide (0.95 parts), anhydrous sodium acetate (1.2 parts), formamide (1.8 parts), acetic anhydride (2.0 parts) and n-butyl acetate (44 parts) are mixed together and heated, with stirring, to 110° C. during 15 minutes. The temperatures is maintained at 110° C. for 31/2 hours when reaction is adjudged complete by thin layer chromatography. The solvent is removed at 80° C. under reduced pressure and the residue is slurried in water (250 parts), collected and dried. 2-Cyano-4-nitro-4'-(N,N-diethylamino)azobenzene is obtained in 75% yield and requires no purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04222935
Source datasetuspto-grants-1980_09
ORD IDord-99c02245faa74ee4a81ad4cfc92bd3be
Source noteuspto-grants-1980_09