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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1589525Generated: November 1, 2026

Dimethylformamide → 4-Chloro-2-(1,1-dimethylethyl)-5-[1-(4-methylphenyl)ethoxy]-3(2H)-pyridazinone

https://huagongshe.com/reaction/1589525

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
Reactant1-(1-Chloroethyl)-4-methylbenzeneHCID 524242—
Reactant2-tert-Butyl-4-chloro-5-hydroxypyridazin-3(2H)-oneHCID 54686946—
SolventWaterHCID 962—
Product4-Chloro-2-(1,1-dimethylethyl)-5-[1-(4-methylphenyl)ethoxy]-3(2H)-pyridazinoneHCID 1559011148.1%

Reaction Steps

1.5 g of anhydrous potassium carbonate and 1.3 g of 4-(α-chloroethyl)toluene were added to 1.5 g of 2-tert.-butyl-4-chloro-5-hydroxy-3(2H)-pyridazinone dissolved into 10 ml of N,N-dimethylformamide, and the resulting mixture was heated under stirring in an oil bath of 80° to 110° C. for 4 hours. After being allowed to cool to room temperature, 100 ml of water was added to the reaction mixture, followed by stirring. Oily matter separated from the reaction mixture was extracted with 50 ml of chloroform. The aqueous layer was extracted with 30 ml of chloroform again, the chloroform layers were combined, washed with water, and dried over anhydrous sodium sulfate. Chloroform was distilled off under reduced pressure, and the residue was recrystallized from isopropyl ether-petroleum ether mixer to obtain 1.1 g of the intended compound (Compound No. 1.78) having m.p. 104°-105.5° C. (yield: 48.1%)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04571397
Source datasetuspto-grants-1986_02
ORD IDord-d316ebea6fcf407aaaaae4c8110d334c
Source noteuspto-grants-1986_02