Nitromethane → 2-amino-1-(2,6-dichlorophenyl)ethan-1-ol
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=[O:5].[N+:11]([CH3:14])([O-])=O>>[NH2:11][CH2:14][CH:4]([OH:5])[C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10]Participants
Procedure
The method of Schoenenberger, Archiv. der Pharmazie, 1975, 308(9), 717-719 can be employed. 2,6-Dichlorobenzaldehyde can be reacted with nitromethane and base, followed by reduction of the aliphatic nitro group to yield 1-amino-2-hydroxy-2-(2,6-dichlorophenyl) ethane. This substance can be reacted with 4-nitrobenzaldehyde to yield a mixture of cis-(±) and trans-(±)-5-(2,6-dichlorophenyl)-2-(4-nitrophenyl)-1,3-oxazolidines. The nitrophenyl group can be reduced with tin (II) dichloride or iron powder and ammonium chloride to yield the corresponding aniline. This aniline can be reacted with 2,2-dichloroacetyl chloride and triethylamine to yield a mixture of cis-(±) and trans-(±)-2,2-dichloro-N-[4-[5-(2,6-dichlorophenyl)-2-(1,3-oxazolidinyl)]phenyl]acetamides.
Sources & evidence
- ORD record
- ord-a6e36625bf504e89b047837d6ec6429d
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07326790B2
Reaction notes
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