Chlorine → HCID 21455747, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][N:11]=[C:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl:19]Cl>C(Cl)(Cl)(Cl)Cl>[Cl:19][C:12]([N:11]=[N:10][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][C:4]=1[Cl:9])([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution consisting of 9.0 g. ethyl pyruvate (2,4,6-trichlorophenyl)hydrazone (mixed isomers) and 100 ml. carbon tetrachloride was chilled to minus 10° (-10° ) C. and 5 ml. chlorine gas was added. After allowing the reaction mixture to warm up to about 25° C., the carbon tetrachloride was removed by evaporation under reduced pressure. The oily residue that remained was dissolved in a mixture of benzene and technical hexane (1 part of benzene to 4 parts of the latter). This solution was poured onto a 50 cm. × 5 cm. column of silica gel and the chromatogram was developed with the solvent mixture. The first portion of eluate was discarded and the fractions containing the orange-red azo compound were saved. After removal of the solvents by evaporation at 100° C. and 10 mm. mercury pressure 6.9 g. ethyl 2-chloro-2-[(2,4,6-trichlorophenyl)azo]propionate was obtained.
Workup
- customthe carbon tetrachloride was removed by evaporation under reduced pressure
- dissolutionThe oily residue that remained was dissolved in a mixture of benzene and technical hexane (1 part of benzene to 4 parts of the latter)
- additionThis solution was poured onto a 50 cm
- additionthe fractions containing the orange-red azo compound
- customAfter removal of the solvents
- customby evaporation at 100° C.
Sources & evidence
- ORD record
- ord-c6617a196791429b88a7af862a978d94
- Source dataset
- uspto-grants-1977_02
- Patent number
- US04006132
Reaction notes
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