1-Chloro-4-(chloromethyl)benzene → 1-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine
Reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.C(NC(C)C)(C)C.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[NH2:11])=[CH:22][CH:21]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension under N2 of 4-methoxyphenylhydrazine hydrochloride (41 g, 230 mmol) in methylene chloride (1000 ml) were added diisopropylamine (79.8 g, 612 mmol), 4-chlorobenzyl chloride (40.25 g, 250 mmol) and tetrabutylammonium bromide (22.8 g, 70 mmol), and the resulting mixture was stirred at room temperature for 48 hours. The reaction mixture was then washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (2.5% methanol/methylene chloride), followed by washing of the solid with 10% ethyl ether in hexane and drying in vacuo to provide 43.5 g of 1-(4-chlorobenzyl)-1-(4-methoxyphenyl)hydrazine. mp.55° C.
Workup
- washThe reaction mixture was then washed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography on silica gel (2.5% methanol/methylene chloride)
- washby washing of the solid with 10% ethyl ether in hexane
- customdrying in vacuo
Sources & evidence
- ORD record
- ord-033cb681b4324a7a82dfee28727d1660
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05399699
Reaction notes
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