Chloroform → 2-oxo-N-phenylpropanehydrazonoyl chloride
Reaction equation
[C:1]1([NH:7][N:8]=[C:9](C(=O)C)[C:10](=[O:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)[Cl:17].ClOC(C)(C)C>CO>[C:1]1([NH:7][N:8]=[C:9]([Cl:17])[C:10]([CH3:11])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
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.
Workup
- customrises to 25° C.
- customNo starting material remains and the solvent of the reaction mixture is evaporated
- customto give a gum, which
- dissolutionis dissolved in 250 ml
- temperatureis then cooled to about 0° C.
- filtrationthe precipitate filtered off
- washwashed with cold methanol
- customportion of this compound is recrystallized from equal parts of ethyl acetate and Skellysolve B (hexanes)
Sources & evidence
- ORD record
- ord-524c3bef95244a879a65fafcb0f5cc27
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03932662
Reaction notes
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