2-oxo-N-phenylpropanehydrazonoyl chloride

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reaction of 951 mg (4.85 mmol) of 1-chloro-1-[(phenyl) hydrazono]-2-propanone with 864 mg of 4-chlorothiophenol and 840 ul of triethylamine in 15 ml of ethanol as Example 11 yielded 347 mg of 1-[(4-chlorophenyl)thio]-1-[(phenyl)hydrazono]-2-propanone, mp 111°-113° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reaction of 10.55 g (0.113 mol)of aminobenzene with 13.2 g of sodium nitrite and 20 g of 3-chloro-2,4-pentanedione as in Example 1 yielded 8.95 g of 1-chloro-1-[(phenyl)hydrazono]-2-propanone, mp 132°-134° C.

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 102.4 g. of 2,3,4-pentanetrione 3-(phenylhydrazone) dissolved in 250 ml. of chloroform and cooled to about 15° C., 100 ml. of tert. butyl hypochlorite is added. The temperature rises to 25° C. and is allowed to cool to 15° C. before the next addition of 60 ml. (0.5 mole). No starting material remains and the solvent of the reaction mixture is evaporated to give a gum, which is dissolved in 250 ml. of methanol and then heated to about 40° C. The temperature of the solution varies from about 40° to about 60° C. for about 15 minutes, and is then cooled to about 0° C., and the precipitate filtered off and washed with cold methanol. The weight of the precipitate that melts at 134° to 136° C. is 71.3 g. (73% yield). A 10 g. portion of this compound is recrystallized from equal parts of ethyl acetate and Skellysolve B (hexanes) to give pure pyruvoyl chloride 1-(phenylhydrazone) melting at 135 to 137° C. rises to 25° C. No starting material remains and the solvent of the reaction mixture is evaporated to give a gum, which is dissolved in 250 ml is then cooled to about 0° C. the precipitate filtered off washed with cold methanol portion of this compound is recrystallized from equal parts of ethyl acetate and Skellysolve B (hexanes)