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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2413100Generated: November 3, 2026

Ammonia → Butanamide, 2-[2-(4-chloro-2-nitrophenyl)diazenyl]-N-(2-chlorophenyl)-3-oxo-

https://huagongshe.com/reaction/2413100

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantChloroacetic AcidHCID 300—
Reactant4-Chloro-2-nitroanilineHCID 6979—
ReactantAcetoacetyl-2-chloroanilideHCID 7156—
ReactantSodium NitriteHCID 23668193—
Solvent2-Ethylhexanoic AcidHCID 8697—
ProductButanamide, 2-[2-(4-chloro-2-nitrophenyl)diazenyl]-N-(2-chlorophenyl)-3-oxo-HCID 94326—

Reaction Steps

8.62 g of p-chloro-o-nitroaniline, 10.89 g of acetoacet-o-chloroanilide, 2.36 g of α-chloroacetic acid and 50 ml of 2-ethylhexanoic acid are stirred at 600 rpm for 1 hour in a 1/2 liter grinding pot containing 200 g of 2-3 mm diameter glass beads. The temperature reaches 26° C. 4.14 g of sodium nitrite are added and stirring continued. As pigment formation commences and the grinding viscosity increases, 25 ml portions of 2-ethylhexanoic acid are added after 2 and 5 minutes. A maximum temperature of 36° C. is obtained after 16 minutes, and after 1 hour, at a temperature of 32° C., aqueous ammonia solution is added and the pigment product recovered, washing well with hot water at the filtration stage. The C.I. Pigment Yellow 3 product, obtained in a yield of 17.84 g (90.3% of theory) is approximately 20% stronger and slightly redder than the corresponding product prepared by conventional aqueous coupling, when dispersed in a decorative alkyd paint system.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04496481
Source datasetuspto-grants-1985_01
ORD IDord-2d776b70ae654642ae45163b1df727bf
Source noteuspto-grants-1985_01