Phosphorus oxychloride → N-(2,4-dichlorophenyl)ethanehydrazonoyl chloride

Temperature

110 °C

A solution of 25.0 grams (0.1142 mole) of 1-acetyl-2-(2,4-dichlorophenyl)-hydrazine (2) in 120 grams of toluene was stirred, and 17.7 grams (0.1142 mole) of phosphorus oxychloride was added portionwise. Upon completion of addition the reaction mixture was warmed to about 110° C. where it stirred for about 30 minutes. GC analysis of the reaction mixture after this time indicated the reaction was complete. An additional 100 grams of toluene was added to the reaction mixture, and the solution was decanted into a separatory funnel. A residue in the reaction vessel was washed with about 40 grams of toluene, and the wash was also decanted into the separatory funnel. The toluene solution was then washed with an aqueous solution of 10% potassium carbonate. The aqueous layer was back-washed with two 75 gram portions of toluene. The combined toluene layer and washes was dried with magnesium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure, yielding 21.3 grams (78.5% yield) of N-(2,4-dichlorophenyl)-ethanehydrazonoyl chloride (A).

1. additionUpon completion of addition the reaction mixture
2. customthe solution was decanted into a separatory funnel
3. washA residue in the reaction vessel was washed with about 40 grams of toluene
4. customthe wash was also decanted into the separatory funnel
5. washThe toluene solution was then washed with an aqueous solution of 10% potassium carbonate
6. washThe aqueous layer was back-washed with two 75 gram portions of toluene
7. dry with materialThe combined toluene layer and washes was dried with magnesium sulfate
8. filtrationThe mixture was filtered
9. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-aea4e46243bb45bd8f95c0585d716a95

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06600049B2