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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 603343Generated: October 25, 2026

Chloroacetyl chloride → N-(2'-Chloro-6'-methylphenyl)-N-chloroacetyl-4-methylaniline

https://huagongshe.com/reaction/603343

Reaction equation

Participants

RoleNameHCIDCharge
ReactantChloroacetyl chlorideHCID 6577—
ReactantN-(2'-chloro-6'-methylphenyl)-4-methylanilineHCID 57952145—
SolventTolueneHCID 1140—
ProductN-(2'-Chloro-6'-methylphenyl)-N-chloroacetyl-4-methylanilineHCID 5795215277.9%

Reaction Steps

The solution of N-(2′-chloro-6′-methylphenyl)-4-methylaniline (1.4 g) in 2.21 g chloroacetylchloride is heated to 90° C. for 4 h. The mixture is diluted with toluene (25 ml), cooled to room temperature and washed with aqu. sodium carbonate. The organic phase is dried, evaporated and the residue is subjected to flash chromatography [57 g silica, toluene and toluene/ethylacetate (98:2)] to afford 1.45 g of N-(2′-Chloro-6′-methylphenyl)-N-chloroacetyl-4-methylaniline which is crystallised from heptane, mp: 113-114° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07906677B2
Source datasetuspto-grants-2011_03
ORD IDord-a3456b5d6a45462da116fb640b9a79d2
Source noteuspto-grants-2011_03