Ethyl Acetoacetate → 55296-56-5
Reaction equation
[C:1]([N:5]=[N:6][C:7]([Cl:15])([CH2:9]CCCCC)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N=NC(Cl)(C)CCC(OCCCC)=O)(C)(C)C.NN.C(OCC)(=O)CC(C)=O.C(NN)(C)(C)C>CC(C)=O>[C:1]([N:5]=[N:6][C:7]([Cl:15])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
Following this procedure, the following α-chloroazos were likewise prepared ("t-BH" is t-butylhydrazone and "t-CH" is t-cumylhydrazone): 2-t-butylazo-2-chlorooctane (in 45.8% crude yield from 2-octanone t-BH), n-butyl 4-t-butylazo-4-chlorovalerate (in 61% crude yield from n-butyl levulinate t-BH), 2-t-cumylazo-2-chloropropane (in 49% crude yield from acetone t-CH prepared by refluxing acetone and an aqueous solution of t-cumylhydrazine, the hydrazine being prepared according to the method of C. G. Overberger et al., J. Am. Chem. Soc. 80, 6562 (1958)), 2-t-cumylazo-2-chloro-4-methylpentane (in 50% crude yield from methyl isobutyl ketone t-CH prepared from methyl isobutyl ketone and t-cumylhydrazine), and ethyl 3-t-butylazo-3-chlorobutirate (in 33.6% crude yield from ethyl acetoacetate t-BH prepared from t-butylhydrazine and ethyl acetoacetate).
Sources & evidence
- ORD record
- ord-68d2e46304f041318197da7616272ab0
- Source dataset
- uspto-grants-1977_09
- Patent number
- US04048423
Reaction notes
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